Supporting Information
|
|
- Augustine Poole
- 5 years ago
- Views:
Transcription
1 Supporting Information Bisebromoamide, a Potent Cytotoxic Peptide from the Marine Cyanobacterium Lyngbya sp.: Isolation, Stereostructure, and Biological Activity Toshiaki Teruya, Hiroaki Sasaki, Hidesuke Fukazawa, and Kiyotake Suenaga * Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi , Kohoku-ku, Yokohama , Japan and National Institute of Infections Diseases, Toyama , Shinjuku-ku, Tokyo , Japan Keio University. National Institute of Infections Diseases. S1
2 Abbreviation of proteins ERK: extracellular signal regulated protein kinase PDGF: platelet-derived growth factor AKT: protein kinase B PKD: protein kinase D PLC: Phospholipase C MEK: MAP kinase/erk kinase MAP: mitogen-activated protein Experimental Procedures and Spectral Data for All New Compounds. General Methods. Chemicals and solvents were the best grade available and were used as received from commercial sources. Optical rotations were measured with a JASCO DIP-360 polarimeter. 1 H NMR spectra were recorded on a JEOL JNM-EX270 (270 MHz) or a JEOL JNM-A400 (400 MHz), instrument. Chemical shifts are reported δ values in parts per million relative to the residual solvent signal (CHD 2 OD: δ = 3.31 ppm; CHCl 3 : δ = 7.26 ppm; for 1 H) and coupling constants are in hertz (Hz). The following abbreviations are used for spin multiplicity: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, and br = broad. 13 C NMR spectra were recorded on a JEOL JNM-A400 (100.4 MHz) instrument using CD 3 OD and CDCl 3 as a solvent, respectively. Chemical shifts are reported in parts per million from the solvent signal (CDCl 3 : δ = 77.2 ppm; CHD 2 OD: δ = 49.0 ppm). The assignments of 1 H NMR and 13 C NMR spectra were determined by H-H COSY, HMQC and HMBC experiments. IR spectra were recorded on a JASCO FT/IR- 410 instrument and are reported in wavenumbers (cm -1 ). ESI mass spectra were recorded on a LCT premier EX spectrometer (Waters). Both TLC analysis and preparative TLC were conducted on E. Merck precoated silical gel 60 F254. Fuji Silysia silica gel BW-820 MH and FL-60D were used for column chromatography unless otherwise noted. Material and method. The marine cyanobacterium Lyngbya sp. was collected at the reef of Bise at 0-1 m depth, Okinawa, Japan (26 4'N, 'E), in April Rat PDGFR-BB is a product of R&D Systems (Minneapolis, MN, USA). Phospho-Akt (Ser473), phospho-pkd/pkcµ (Ser 916), phospho-erk1/2 (Thr202/Tyr204), phosphop90rsk (Thr359/S363) and phospho-s6 ribosomal protein (Ser 235/236) antibodies were acquired from Cell Signaling Technology, Inc (Danvers, MA, USA). Immunoblotting analysis. To observe effects on PDGF-signaling, NRK (normal rat kidney) cells were seeded in 96-well plates in a volume of 100 µl at a density of cells per well, cultured for 2 days, and then serum starved for 24 h. Cells were treated with inhibitors for 3 h and stimulated with 50 ng/ml rat PDGF-BB for 10 min. Cells were fixed for 10 min with 10% cold trichloroacetic acid and lysed with 9 M urea, 2% Triton X-100 and 2% lithium dodecyl sulfate. Lysates were neutralized with 2 M Tris and passed through a syringe to reduce viscosity. Proteins were subjected to SDS-PAGE and analyzed by immunoblotting using a cocktail that contained antibodies against phosphorylated forms of the components of the PKC pathway (phospho-pkd), the PI3K-AKT pathway (phospho-akt, phospho-s6r) and the MEK-ERK pathway (phospho-erk and phospho-p90rsk). Extraction and isolation. Approximately 1300 g (wet weight) of cyanobacterium was extracted with methanol (3 L) for one week. The extract was filtered, and the filtrate was concentrated. The residue was partitioned between ethyl acetate (3 0.3 L) and water (0.3 L). The material obtained from the organic S2
3 layer were partitioned between 90% aqueous methanol and hexane. The aqueous methanol fraction (0.36 g) was first separated by column chromatography on ODS (6 g) using 40% methanol, 60% methanol, 80% methanol, and methanol. The fraction (41 mg) eluted with 80% methanol was subjected to HPLC [Cosmosil 5C 18 -AR-II (φ mm); flow rate 5mL/min; detection, UV 215 nm; solvent 65% MeCN] to give bisebromoamide (1) (9.6 mg, t R = 36.5 mim): [α] 22 D (c 1.00, CHCl 3 ); IR (CHCl 3 ) 3522, 3436, 3328, 1640 cm H NMR Data for bisebromoamide (1; 400 MHz, CDCl 3 ). δ 7.47 (d, J = 6.8 Hz, 1H), 7.31 (d, J = 2.0 Hz, 1H), 7.20 (d, J = 7.3, 1.5 Hz, 2H), 7.13 (dd, J = 7.8, 7.3 Hz, 2H), 7.09 (dd, J = 7.8, 1.5 Hz, 1H), 7.07 (d, J = 8.3, 2.0 Hz, 1H), 6.84 (d, J = 8.3 Hz, 1H), 6.37 (d, J = 7.8 Hz, 1H), 5.83 (dd, J = 11.2, 5.9 Hz, 1H), 5.59 (dd, J = 9.3, 7.8 Hz, 1H), 4.87 (dd, J = 10.7, 7.3 Hz, 1H), 4.70 (m, 1H), 4.56 (dd, J = 8.8, 3.9 Hz, 1H), 4.50 (m, 1H), 3.54 (m, 2H), 3.52 (m, 1H), 3.39 (d, J = 11.2 Hz, 1H), 3.14 (s, 3H), 3.10 (d, J = 11.2 Hz, 1H), 3.06 (s, 3H), 3.06 (m, 2H), 3.05 (m, 2H), 2.89 (m, 1H), 2.54 (m, 1H), 2.50 (m, 1H), 2.35 (m, 1H), 2.19 (m, 1H), 2.11 (m, 1H), 1.88 (m, 2H), 1.80 (m, 1H), 1.74 (m, 1H), 1.55 (s, 3H), 1.43 (m, 1H), 1.41 (m, 1H), 1.17 (s, 9H), 1.07 (t, J = 7.3 Hz, 3H), 1.03 (d, J = 5.9 Hz, 3H), 0.87 (d, J = 7.3 Hz, 3H), 0.76 (d, J = 6.8 Hz, 3H), 0.74 (d, J = 6.8 Hz, 3H), 0.54 (m, 1H). Acid hydrolysis of 1. Bisebromoamide 1 (500 µg, 0.49 µmol) and 9 M HCl (0.1 ml) was charged in a reaction tube, and sealed up under reduced pressure. The mixture was heated at 110 for 72 h, diluted with water (1 ml), and evaporated. The acid hydrolysate could be separated into each components except for a mixture of Ala and 2-methylcystine. [Condition for the HPLC separation: column, Cosmosil 5C 18 -PAQ ( mm); solvent, MeOH/H 2 O = 5/95; flow rate, 1.0 ml/min; detection at 254 nm. The retention times (min) of components: Ala and 2-methylcystine (3.6), Leu (3.9), N-Me-Tyr (7.0), N-Me-Phe(10.8)]. Conditions for chiral HPLC analyses of Leu, N-Me-Tyr, N-Me-Phe. Leu: column, CHIRALPAK(MA+) ( mm); solvent, 2mM CuSO 4 ; flow rate, 1.0 ml/min; detection at 254 nm. t R (min) Authentic samples : D-Leu (7.5), L-Leu (13.2). Leu from natural 1: Leu (7.5). Authentic D,L-Leu Leu from natural 1 S3
4 N-Me-Tyr: column, CHIRALPAK(MA+) ( mm); solvent, MeOH/2 mm CuSO 4 = 95/5; flow rate, 0.5 ml/min; detection at 254 nm. t R (min) Authentic samples : N-Me-D-Tyr (11.3), N-Me-L-Tyr (14.1). N-Me-Tyr from natural 1: N-Me-Tyr (11.3). Authentic N-Me-D,L-Tyr N-Me-Tyr from natural 1 N-Me-Phe: column, CHIRALPAK(MA+) ( mm); solvent, MeCN/2 mm CuSO 4 = 90/10; flow rate, 0.5 ml/min; detection at 254 nm. t R (min) Authentic samples : N-Me-D-Phe (11.3), N-Me-L-Phe (12.5). N-Me-Phe from natural 1: N-Me-Phe (12.5). Authentic N-Me-D,L-Phe N-Me-Phe from natural 1 S4
5 Conditions for HPLC analyses of Marfey derivatives of Ala and 2-methylcystine. Ala: column, Cosmosil 5C 18 -AR-II ( mm); solvent, MeOH/0.02 M AcONa =65/35; flow rate, 1.0 ml/min; detection at 340 nm. t R (min) Marfey derivatives of authentic samples : D-Ala (9.2), L-Ala (5.0). Marfey derivatives of Ala from natural 1: Ala (5.0). Marfey derivatives of authentic L-Ala Ala from natural 1 2-Methylcystine: column, Cosmosil 5C 18 -MS-II ( mm); solvent, MeOH/0.02 M AcONa =60/40; flow rate, 1.0 ml/min; detection at 340 nm. t R (min) Marfey derivatives of authentic samples : D-2-Methylcystine (5.9), L-2-Methylcystine (8.8). Marfey derivatives of 2-Methylcystine from natural 1: 2-Methylcystine (5.9). Marfey derivatives of authentic D-2-Methylcystine Marfey derivatives of authentic L-2-Methylcystine S5
6 Marfey derivatives of 2-Methylcystine from natural 1 1 O 3 then aq. HCl 4 N H 2 COOH 7:3 Ozonolysis-acid hydrolysis of 1. Ozone gas was bubbled through a solution of bisebromoamide 1 (4.0 mg, 3.9 µmol) in MeOH (4 ml) for 30 min at -78. Excess ozone was evacuated by bubbling nitrogen, and dimethyl sulfide (0.1 ml) was added. The mixture was warmed to room temperature and concentrated to give an colorless oil. This oil and 9 M HCl (0.1 ml) was charged in a reaction tube, and sealed up under reduced pressure. The mixture was heated at 110 for 48 h, diluted with water (1 ml), and evaporated. The residue was purified by reversed phase HPLC to afford components, Me-Pro [2S : 2R = 7:3 from 1 H NMR and HPLC analysis of Marfey derivatives, see below]. [Condition for the HPLC separation: column, Cosmosil 5C 18 -PAQ ( mm); solvent, MeOH/H 2 O/TFA = 1/99/0.1; flow rate, 5.0 ml/min; detection at 215 nm. The retention time (min) of components: Me-Pro (21.8)]. From 1 H NMR data, the relative stereochemistry of two stereoisomers were established. The major isomer was assigned as cis-4- methylproline and minor isomer was assigned as trans-4-methylproline. + 4 N H 2 COOH S6
7 Conditions for HPLC analysis of Marfey derivatives of 4-Me-Pro. 4-Me-Pro: column, Cosmosil 5C 18 -MS-II ( mm); solvent, MeOH/0.02 M AcONa =70/30; flow rate, 1.0 ml/min; detection at 340 nm. t R (min) Marfey derivatives of authentic samples : (2S, 4S)-4-Me-Pro (4.5), (2R, 4R)-4-Me-Pro (8.0). Marfey derivatives of 4-Me-Pro from natural 1: 4-Me-Pro (4.5, 8.0). The ratio of peak intensity is 7:3. Authentic (2S, 4S)-4-Me-Pro and 4-Me-Pro from natural 1 4-Me-Pro from natural 1 S7
8 1 H NMR spectrum of Me-Pro from natural 1 [400 MHz, D 2 O]. S8
9 8 8 1 NaBH 4 then aq. HCl HO HN 2 + HO HN 2 5 1:1 Reduction-acid hydrolysis of 1. To a stirred solution of 1 (3.5 mg, 3.4 µmol) in MeOH (0.5 ml) at room temperature was added sodium borohydride (30 mg, 0.79 mmol). After being stirred at room temperature for 2 h, the mixture was diluted with AcOEt (5 ml) and H 2 O (5 ml), successively. The organic layer was separated, and the aqueous layer was extracted with AcOEt (2 10 ml). The organic layer and the extracts were combined, washed with saturated aqueous NaCl (15 ml), dried (Na 2 SO 4 ), and concentrated. The residual oil (3.3 mg, 3.2 µmol) and 9 M HCl (0.1 ml) was charged in a reaction tube, and sealed up under reduced pressure. The mixture was heated at 110 for 48 h, diluted with water (1 ml), and evaporated. The residue was purified by reversed phase HPLC to afford components, 2-(1-hydroxypropyl)- piperidine [6S : 6R = 1:1]. [Condition for the HPLC separation: column, Cosmosil 5C 18 -PAQ ( mm); solvent, MeOH/H 2 O/TFA = 1/99/0.1; flow rate, 5.0 ml/min; detection at 215 nm. The retention times (min) of components: 2-(1-hydroxypropyl)-piperidine (33.9)]. The absolute stereochemistry of C6 was not determined. Conditions for HPLC analyses of Marfey derivatives of 2-(1-hydroxypropyl)-piperidine. 2-(1-hydroxypropyl)-piperidine: Condition 1. column, Cosmosil 5C 18 -MS-II ( mm); solvent, MeOH/0.02 M AcONa =70/30; flow rate, 1.0 ml/min; detection at 340 nm. t R (min) Marfey derivatives of authentic samples : 2(R)-(1-hydroxypropyl)-piperidine [6S : 6R = 1:1] (9.7, 3.3), 2(S)- (1-hydroxypropyl)-piperidine [6S : 6R = 1:1] (15.3, 3.3). Marfey derivatives of 2-(1-hydroxypropyl)-piperidine from natural 1: 2-(1-hydroxypropyl)-piperidine (15.3, 3.3). 5 2-(1-hydroxypropyl)-piperidine from natural 1 Authentic 2(S) and from natural 1 S9
10 Although the retention time of one diastereomer of Marfey derivatives of authentic samples was identical to that from natural 1 (retention time : 15.3 min), two diastereomers of Marfey derivatives of authentic samples could not be separated above condition (retention time : 3.3 min). These diastereomers could be separated under the following conditions. Condition 2. column, Cosmosil 5C 18 -MS-II ( mm); solvent, MeCN/0.02 M AcONa =40/60; flow rate, 1.0 ml/min; detection at 340 nm. t R (min) Marfey derivatives of authentic samples : 2(R)-(1-hydroxypropyl)-piperidine [6S : 6R = 1:1] (33.4), 2(S)-(1- hydroxypropyl)-piperidine [6S : 6R = 1:1] (30.4). Marfey derivatives of 2-(1-hydroxypropyl)-piperidine from natural 1: 2-(1-hydroxypropyl)-piperidine (30.4). Authentic 2(R) and from natural 1 Authentic 2(S) and from natural 1 Although one diastereomer of Marfey derivatives of authentic samples could not be detected under the condition 2, the retention time of one diastereomer of Marfey derivative of authentic sample was identical to that from natural 1 (retention time : 30.4 min). S10
11 1 H NMR spectrum of 1 [400 MHz, CD 3 OD]. S11
12 1 H NMR spectrum of 1 [400 MHz, CDCl 3 ]. S12
13 13 C NMR spectrum of 1 [100 MHz, CD 3 OD]. S13
14 COSY spectrum of 1 [400 MHz, CD 3 OD]. S14
15 HMQC spectrum of 1 [400 MHz, CD 3 OD]. S15
16 HMBC spectrum of 1 [400 MHz, CD 3 OD]. S16
17 GI 50 values of bisebromoamide (1) against 39 human cancer cell lines Type of cancer Cell line GI 50 a,b (nm) Breast HBC-4 97 BSY-1 24 HBC-5 27 MCF-7 35 MDA-MB Central nervous system U SF SF SF SNB SNB Colon HCC KM HT HCT HCT Lung NCI-H23 92 NCI-H NCI-H NCI-H A DMS DMS Melanoma LOX-IMVI 26 Ovary OVCAR-3 28 OVCAR-4 27 OVCAR OVCAR SK-OV-3 86 Kidney RXF-631L 36 ACHN 32 Stomach St-4 19 MKN1 24 MKN7 13 MKN28 MKN MKN74 34 Prostate DU PC MG-MID c 40 Delta d 0.49 Range e 0.89 a Concentrations for the inhibition of cell growth at 50% relative to control. b Cell growth was determined according to the sulforhodamine B assay. c Mean GI 50 value in all of the cell lines tested. d Difference in the GI 50 value between the most-sensitive cells and the MG-MID value. e Difference in the log GI 50 value between the most- and least-sensitive cells. S17
Masatoshi Shibuya,Takahisa Sato, Masaki Tomizawa, and Yoshiharu Iwabuchi* Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences,
Oxoammonium ion/naclo 2 : An Expedient, Catalytic System for One-pot Oxidation of Primary Alcohols to Carboxylic Acid with Broad Substrate Applicability Masatoshi Shibuya,Takahisa Sato, Masaki Tomizawa,
More informationTHE JOURNAL OF ANTIBIOTICS. Polyketomycin, a New Antibiotic from Streptomyces sp. MK277-AF1. II. Structure Determination
THE JOURNAL OF ANTIBIOTICS Polyketomycin, a New Antibiotic from Streptomyces sp. MK277-AF1 II. Structure Determination ISAO MOMOSE, WEI CHEN, HIKARU NAKAMURA, HIROSHI NAGANAWA, HIRONOBU IINUMA and TOMIO
More informationManganese powder promoted highly efficient and selective synthesis of fullerene mono- and biscycloadducts at room temperature
Supplementary Information Manganese powder promoted highly efficient and selective synthesis of fullerene mono- and biscycloadducts at room temperature Weili Si 1, Xuan Zhang 1, Shirong Lu 1, Takeshi Yasuda
More informationZinc Chloride Promoted Formal Oxidative Coupling of Aromatic Aldehydes and Isocyanides to α- Ketoamides
Supporting information for Zinc Chloride Promoted Formal xidative Coupling of Aromatic Aldehydes and Isocyanides to α- Ketoamides Marinus Bouma, Géraldine Masson* and Jieping Zhu* Institut de Chimie des
More informationPreparation of Fluorinated Tetrahydropyrans and Piperidines using a New Nucleophilic Fluorination Reagent DMPU/HF
Supporting information Preparation of Fluorinated Tetrahydropyrans and Piperidines using a New Nucleophilic Fluorination Reagent DMPU/HF Otome E. Okoromoba, a Gerald B. Hammond, a, * Bo Xu b, * a Department
More informationSupporting information
Supporting information Diversity Oriented Asymmetric Catalysis (DOAC): Stereochemically Divergent Synthesis of Thiochromanes Using an Imidazoline-aminophenol aminophenol (IAP)-Ni Catalyzed Michael/Henry
More informationStereoselective Aza-Darzens Reactions of Tert- Butanesulfinimines: Convenient Access to Chiral Aziridines
Stereoselective Aza-Darzens Reactions of Tert- Butanesulfinimines: Convenient Access to Chiral Aziridines Toni Moragas Solá, a Ian Churcher, b William Lewis a and Robert A. Stockman* a Supplementary Information
More informationPreparation of Stable Aziridinium Ions and Their Ring Openings
Supplementary Information Preparation of Stable Aziridinium Ions and Their Ring Openings Yongeun Kim a Hyun-Joon Ha*, a Sae Young Yun b and Won Koo Lee,*,b a Department of Chemistry and Protein Research
More informationSupporting Information
Supporting Information Unconventional Passerini Reaction towards α-aminoxyamides Ajay L. Chandgude, Alexander Dömling* Department of Drug Design, University of Groningen, Antonius Deusinglaan 1, 9713 AV
More informationRameshwar Prasad Pandit and Yong Rok Lee * School of Chemical Engineering, Yeungnam University, Gyeongsan , Korea
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Novel ne-pot Synthesis of Diverse γ,δ-unsaturated β-ketoesters by Thermal
More informationp-toluenesulfonic Acid-Mediated 1,3-Dipolar Cycloaddition of
Supporting Information for: p-toluenesulfonic Acid-Mediated 1,3-Dipolar Cycloaddition of Nitroolefins with NaN 3 for Synthesis of 4-Aryl-NH-1,2,3-triazoles Xue-Jing Quan, Zhi-Hui Ren, Yao-Yu Wang, and
More informationFacile Cu(II) mediated conjugation of thioesters and thioacids to peptides and proteins under mild conditions
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Facile Cu(II) mediated conjugation of thioesters and thioacids to peptides
More informationSupporting Information. Recyclable hypervalent-iodine-mediated solid-phase peptide
Supporting Information Recyclable hypervalent-iodine-mediated solid-phase peptide synthesis and cyclic peptide synthesis Dan Liu, Ya-Li Guo, Jin Qu and Chi Zhang* for Address: State Key Laboratory of Elemento-Organic
More informationElectronic Supplementary Information. Quinine/Selectfluor Combination Induced Asymmetric Semipinacol Rearrangement of
Electronic Supplementary Information Quinine/Selectfluor Combination Induced Asymmetric Semipinacol Rearrangement of Allylic Alcohols: An Effective and Enantioselective Approach to α Quaternary β Fluoro
More informationSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Supporting Information Enantioselective Cu-catalyzed 1,4-Addition of Various Grignard Reagents to Cyclohexenone using Taddol-derived Phosphine-Phosphite
More informationSupplementary Materials Contents
Supplementary Materials Contents Supporting information... S1 1. General Information & Materials... S2 2. General Procedure for ptimization of Amidation of Aryl Bromides with Copper/,-Dimethylglycine Catalytic
More informationSupplementary Information
Supplementary Information J. Braz. Chem. Soc., Vol. 24, No. 12, S1-S21, 2013. Printed in Brazil - 2013 Sociedade Brasileira de Química 0103-5053 $6.00+0.00 SI Rui He, a,b,c Bochu Wang,*,b Toshiyuki Wakimoto,
More informationSupporting Materials. Experimental Section. internal standard TMS (0 ppm). The peak patterns are indicated as follows: s, singlet; d,
CuBr-Catalyzed Efficient Alkynylation of sp 3 C-H Bonds Adjacent to a itrogen Atom Zhiping Li and Chao-Jun Li* Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, Quebec H3A
More informationL-Carnosine-Derived Fmoc-Tripeptides Forming ph- Sensitive and Proteolytically Stable Supramolecular
Supporting Information: L-Carnosine-Derived Fmoc-Tripeptides Forming ph- Sensitive and Proteolytically Stable Supramolecular Hydrogels Rita Das Mahapatra, a Joykrishna Dey* a, and Richard G. Weiss b a
More informationThiol-Activated gem-dithiols: A New Class of Controllable. Hydrogen Sulfide (H 2 S) Donors
Thiol-Activated gem-dithiols: A New Class of Controllable Hydrogen Sulfide (H 2 S) Donors Yu Zhao, Jianming Kang, Chung-Min Park, Powell E. Bagdon, Bo Peng, and Ming Xian * Department of Chemistry, Washington
More informationNitro-Grela-type complexes containing iodides. robust and selective catalysts for olefin metathesis
Supporting Information for Nitro-Grela-type complexes containing iodides robust and selective catalysts for olefin metathesis under challenging conditions. Andrzej Tracz, 1,2 Mateusz Matczak, 1 Katarzyna
More informationSupporting Information. An Efficient Synthesis of Optically Active Physostigmine from Tryptophan via Alkylative Cyclization
Supporting Information An Efficient Synthesis of Optically Active Physostigmine from Tryptophan via Alkylative Cyclization Michiaki, Kawahara, Atsushi Nishida, Masako Nakagawa* Faculty of Pharmaceutical
More informationNovel D-erythro N-Octanoyl Sphingosine Analogs As Chemo- and Endocrine. Resistant Breast Cancer Therapeutics
Page 11 of 32 Cancer Chemotherapy and Pharmacology Novel D-erythro N-Octanoyl Sphingosine Analogs As Chemo- and Endocrine Resistant Breast Cancer Therapeutics James W. Antoon, Jiawang Liu, Adharsh P. Ponnapakkam,
More informationNaoya Takahashi, Keiya Hirota and Yoshitaka Saga* Supplementary material
Supplementary material Facile transformation of the five-membered exocyclic E-ring in 13 2 -demethoxycarbonyl chlorophyll derivatives by molecular oxygen with titanium oxide in the dark Naoya Takahashi,
More informationChukvelutins A-C, 16-norphragmalin limonoids with unprecedented skeletons from Chukrasia tabularis var. velutina
Chukvelutins A-C, 16-norphragmalin limonoids with unprecedented skeletons from Chukrasia tabularis var. velutina Jun Luo, Jun-Song Wang, Jian-Guang Luo, Xiao-Bing Wang, and Ling-Yi Kong* Department of
More informationPreparation, isolation and characterization of N α -Fmoc-peptide isocyanates: Solution synthesis of oligo-α-peptidyl ureas
SUPPORTING INFORMATION Preparation, isolation and characterization of N α -Fmoc-peptide isocyanates: Solution synthesis of oligo-α-peptidyl ureas Vommina V. Suresh Babu*, Basanagoud S. Patil, and Rao Venkataramanarao
More informationSupporting Information
Notes Bull. Korean Chem. Soc. 2013, Vol. 34, No. 1 1 http://dx.doi.org/10.5012/bkcs.2013.34.1.xxx Supporting Information Chemical Constituents of Ficus drupacea Leaves and their α-glucosidase Inhibitory
More informationSupporting Information
Electronic Supplementary Material (ESI) for rganic Chemistry Frontiers. This journal is the Partner rganisations 2016 Supporting Information Fangyi Li, Changgui Zhao, and Jian Wang* Department of Pharmacology
More informationRegioective Halogenation of 2-Substituted-1,2,3-Triazole via sp 2 C-H Activation
Regioective Halogenation of 2-Substituted-1,2,3-Triazole via sp 2 C-H Activation Qingshan Tian, Xianmin Chen, Wei Liu, Zechao Wang, Suping Shi, Chunxiang Kuang,* Department of Chemistry, Tongji University,
More informationElectronic Supplementary Information
Electronic Supplementary Information ~ Experimental Procedures and Spectral/Analytical Data ~ Use of Dimethyl Carbonate as a Solvent Greatly Enhances the Biaryl Coupling of Aryl Iodides and Organoboron
More informationSolid Phase Peptide Synthesis (SPPS) and Solid Phase. Fragment Coupling (SPFC) Mediated by Isonitriles
Solid Phase Peptide Synthesis (SPPS) and Solid Phase Fragment Coupling (SPFC) Mediated by Isonitriles Ting Wang a and Samuel J. Danishefsky a,b,* alaboratory for Bioorganic Chemistry, Sloan- Kettering
More informationSupporting Information. Total Synthesis of Grandisine D. Haruaki Kurasaki, Iwao Okamoto, Nobuyoshi Morita, and Osamu Tamura*
Supporting Information Total Synthesis of Grandisine D Haruaki Kurasaki, Iwao Okamoto, Nobuyoshi Morita, and Osamu Tamura* Discovery Research Laboratories, Kyorin Pharmaceutical Co. Ltd. 2399-1, Nogi,
More informationEnantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction
Enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction P. Veeraraghavan Ramachandran* and Prem B. Chanda Department of Chemistry, Purdue
More informationSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007 Organocatalytic Asymmetric Sulfa-Michael Addition to α,β- Unsaturated Ketones Paolo Ricci, Armando Carlone, Giuseppe
More informationSupporting Information. for. Synthesis of dye/fluorescent functionalized. dendrons based on cyclotriphosphazene
Supporting Information for Synthesis of dye/fluorescent functionalized dendrons based on cyclotriphosphazene Aurélien Hameau 1,2, Sabine Fuchs 1,2, Régis Laurent 1,2, Jean-Pierre Majoral* 1,2 and Anne-Marie
More informationSupporting Information for. Boronic Acid Functionalized Aza-Bodipy (azabdpba) based Fluorescence Optodes for the. analysis of Glucose in Whole Blood
Supporting Information for Boronic Acid Functionalized Aza-Bodipy (azabdpba) based Fluorescence Optodes for the analysis of Glucose in Whole Blood Yueling Liu, Jingwei Zhu, Yanmei Xu, Yu Qin*, Dechen Jiang*
More informationEthyl 2-hydroxy-4-methyl-1-((prop-2-yn-1-yloxy)methyl)cyclohex-3-enecarboxylate (16):
General methods: 1 H NMR and 13 C NMR spectra were recorded in CDCl 3 or CDCl3 and CCl 4 as solvent on 300 MHz or 500 MHz spectrometer at ambient temperature. The coupling constant J is given in Hz. The
More informationSynthesis and Blastocyst Implantation Inhibition Potential of Lupeol Derivatives in Female Mice
Supporting Information Rec. Nat. Prod. 9:4 (2015) 561-566 Synthesis and Blastocyst Implantation Inhibition Potential of Lupeol Derivatives in Female Mice Anita Mahapatra 1*, Purvi Shah 1, Mehul Jivrajani
More information2,6,9-Triazabicyclo[3.3.1]nonanes as overlooked. amino-modification products by acrolein
Supplementary Information 2,6,9-Triazabicyclo[3.3.1]nonanes as overlooked amino-modification products by acrolein Ayumi Tsutsui and Katsunori Tanaka* Biofunctional Synthetic Chemistry Laboratory, RIKEN
More informationGraduate School of Nutritional and Environmental Sciences, University of Shizuoka,
Identification of Indole Alkaloid Structural Units Important for Stimulus Selective TRPM8 Inhibition: SAR Study of Naturally Occurring Iboga Derivatives Yuko Terada,, Mariko Kitajima,, Fuyumi Taguchi,
More informationSupplementary Materials
A Case of Remote Asymmetric Induction in the Peptide-Catalyzed Desymmetrization of a Bis(phenol) Chad A. Lewis, Jeffrey L. Gustafson, Anna Chiu, Jaume Balsells, David Pollard, Jerry Murry, Robert A. Reamer,
More informationSupporting Information
Supporting Information Developing novel activity-based fluorescent probes that target different classes of proteases Qing Zhu, Aparna Girish, Souvik Chattopadhaya and Shao Q Yao * Departments of Chemistry
More informationAnalysis of fatty acid metabolism using Click-Chemistry and HPLC-MS
Analysis of fatty acid metabolism using Click-Chemistry and HPLC-MS Alexander J. Pérez and Helge B. Bode -Supporting Information- Contents Experimental section Supplementary figures NMR spectra Page S2
More informationOrganic Letters. Synthesis of Oxygen-Free [2]Rotaxanes: Recognition of Diarylguanidinium Ions by Tetraazacyclophanes. and Sheng-Hsien Chiu*
Organic Letters Synthesis of Oxygen-Free [2]Rotaxanes: Recognition of Diarylguanidinium Ions by Tetraazacyclophanes Yu-Hsuan Chang, Yong-Jay Lee, Chien-Chen Lai, Yi-Hung Liu, Shie-Ming Peng, and Sheng-Hsien
More informationSUPPLEMENTARY MATERIAL
SUPPLEMENTARY MATERIAL Chemical constituents from Agrimonia pilosa Ledeb. and their chemotaxonomic significance Wei-jie Liu, Xue-qian Hou, Hao Chen, Jing-yu Liang*, Jian-bo Sun** Department of Natural
More informationSupporting Information Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C C Bond Cleavage of 2-Arylin
Supporting Information Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C C Bond Cleavage of 2-Arylindoles Wei-Li Chen, Si-Yi Wu, Xue-Ling Mo, Liu-Xu Wei,
More informationSupporting Information
Ferrocene Amino Acid Macrocycles as Hydrazone Based Receptors for Anions Sophie R. Beeren and Jeremy K. M. Sanders Supporting Information S1 Experimental 2 S1.1 General Experimental Procedures 2 S1.2 Synthesis
More informationDivergent Construction of Pyrazoles via Michael Addition of N-Aryl Hydrazones to 1,2-Diaza-1,3-dienes
Divergent Construction of Pyrazoles via Michael Addition of N-Aryl Hydrazones to 1,2-Diaza-1,3-dienes Serena Mantenuto, Fabio Mantellini, Gianfranco Favi,* and Orazio A. Attanasi Department of Biomolecular
More informationSupporting Information
Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2011 Supporting Information Potassium tert-butoxide Mediated Heck-Type Cyclization/Isomerization
More informationCatalytic decarboxylative alkylation of β-keto acids with sulfonamides via the cleavage of carbon nitrogen and carbon carbon bonds
Catalytic decarboxylative alkylation of β-keto acids with sulfonamides via the cleavage of carbon nitrogen and carbon carbon bonds Cui-Feng Yang, Jian-Yong Wang and Shi-Kai Tian* Joint Laboratory of Green
More informationSupplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2008
Experimental Details Unless otherwise noted, all chemicals were purchased from Sigma-Aldrich Chemical Company and were used as received. 2-DOS and neamine were kindly provided by Dr. F. Huang. Paromamine
More informationImproved Carbonylation of Heterocyclic Chlorides and Challenging Aryl Bromides
Albaneze-Walker et al S-1 Improved Carbonylation of Heterocyclic Chlorides and Challenging Aryl Bromides Jennifer Albaneze-Walker*, Charles Bazaral, Tanya Leavey, Peter G. Dormer, and Jerry A. Murry Department
More informationLewis acid-catalyzed regioselective synthesis of chiral α-fluoroalkyl amines via asymmetric addition of silyl dienolates to fluorinated sulfinylimines
Supporting Information for Lewis acid-catalyzed regioselective synthesis of chiral α-fluoroalkyl amines via asymmetric addition of silyl dienolates to fluorinated sulfinylimines Yingle Liu a, Jiawang Liu
More informationSupporting Information
Supporting Information Asymmetric organocatalytic formation of protected and unprotected tetroses under potentially prebiotic conditions. Laurence Burroughs, Paul A. Clarke,* Henrietta Forintos, James
More informationSupporting Information
Supporting Information Asperphenins A and B, Lipopeptidyl Benzophenones from a Marinederived Aspergillus sp. Fungus Lijuan Liao, Song Yi Bae, Tae Hyung Won, Minjung You, Seong-Hwan Kim, Dong-Chan Oh, Sang
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information [Fe III (TF4DMAP)OTf] Catalysed Anti-Markovnikov Oxidation
More informationSupporting Information for. Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of. 3,5-Disubstituted Pyridines: Mechanistic Studies
Supporting Information for Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of 3,5-Disubstituted Pyridines: Mechanistic Studies Ta-Hsien Chuang* a, Yu-Chi Chen b and Someshwar Pola
More informationEfficient Metal-Free Pathway to Vinyl Thioesters with Calcium Carbide as the Acetylene Source
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information Efficient Metal-Free Pathway to Vinyl Thioesters with Calcium Carbide
More informationFluorescent probes for detecting monoamine oxidase activity and cell imaging
Fluorescent probes for detecting monoamine oxidase activity and cell imaging Xuefeng Li, Huatang Zhang, Yusheng Xie, Yi Hu, Hongyan Sun *, Qing Zhu * Supporting Information Table of Contents 1. General
More informationph Switchable and Fluorescent Ratiometric Squarylium Indocyanine Dyes as Extremely Alkaline Sensors
ph Switchable and Fluorescent Ratiometric Squarylium Indocyanine Dyes as Extremely Alkaline Sensors Jie Li, Chendong Ji, Wantai Yang, Meizhen Yin* State Key Laboratory of Chemical Resource Engineering,
More informationStudent Handout. This experiment allows you to explore the properties of chiral molecules. You have
Student Handout This experiment allows you to explore the properties of chiral molecules. You have learned that some compounds exist as enantiomers non-identical mirror images, such as your left and right
More informationSynthesis of cationic porphyrin modified amino. acids
Synthesis of cationic porphyrin modified amino acids Eric Biron and Normand Voyer* Département de chimie and CREFSIP, Faculté des sciences et de génie, Université Laval, Québec, Québec, Canada G1K 7P4
More informationSupporting Information. Radical fluorination powered expedient synthesis of 3 fluorobicyclo[1.1.1]pentan 1 amine
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information Radical fluorination powered expedient synthesis
More informationStructure and conserved function of iso-branched sphingoid bases from the nematode Caenorhabditis elegans
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 207 Structure and conserved function of iso-branched sphingoid bases from the nematode Caenorhabditis
More informationThe First Au-Nanoparticles Catalyzed Green Synthesis of Propargylamines Via Three-Component Coupling Reaction of Aldehyde, Alkyne And Amine
Supporting information of The First Au-anoparticles Catalyzed Green Synthesis of Propargylamines Via Three-Component Coupling Reaction of Aldehyde, Alkyne And Amine Mazaahir Kidwai a *, Vikas Bansal a,
More informationHighly enantioselective tandem enzyme-organocatalyst crossed aldol reactions. with acetaldehyde in deep-eutectic-solvents.
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Highly enantioselective tandem enzyme-organocatalyst crossed aldol reactions with acetaldehyde
More informationSupporting Information
HYDRAmers: Design, synthesis and characterization of different generation novel Hydra-like dendrons based on multifunctionalized adamantane Giuseppe Lamanna,* Julie Russier, Cécilia Ménard-Moyon, and Alberto
More informationSupporting Information
Supporting Information Synthesis of N-Heteropolycyclic Compounds Including Quinazolinone Skeletons by Using Friedel-Crafts Alkylation Bu Keun Oh, Eun Bi Ko, Jin Wook Han* and Chang Ho Oh* Department of
More informationSupporting Information
J. Am. Chem. Soc. Supporting Information S 1 Enantioselective rganocatalytic Indole Alkylations. Design of a New and Highly Effective Chiral Amine for Iminium Catalysis. Joel F. Austin and David W. C.
More informationSupporting Information
Supporting Information B(C 6 F 5 ) 3 -catalyzed Regioselective Deuteration of Electronrich Aromatic and Heteroaromatic compounds Wu Li, Ming-Ming Wang, Yuya Hu and Thomas Werner* Leibniz-Institute of Catalysis
More informationSupporting Information: Cis-to-Trans Isomerization of Azobenzene Investigated by Using Thin Films of Metal-Organic Frameworks
Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. This journal is the wner Societies 2015 Supporting Information: Cis-to-Trans Isomerization of Azobenzene Investigated by
More informationReaction of difluorocarbene with acetylene ethers generates novel fluorinated 5- and 7-membered carbacycles.
Electronic Supplementary Information (ESI) Reaction of difluorocarbene with acetylene ethers generates novel fluorinated 5- and 7-membered carbacycles. Poh Wai Chia, Davide Bello, Alexandra M. Z. Slawin
More informationSupplemental Material
Supplemental Material General Methods Unless otherwise indicated, all anhydrous solvents were commercially obtained and stored under nitrogen. Reactions were performed under an atmosphere of dry nitrogen
More informationDirect Aerobic Carbonylation of C(sp 2 )-H and C(sp 3 )-H Bonds through Ni/Cu Synergistic Catalysis with DMF as the Carbonyl Source
Direct Aerobic Carbonylation of C(sp 2 )-H and C(sp 3 )-H Bonds through Ni/Cu Synergistic Catalysis with DMF as the Carbonyl Source Xuesong Wu, Yan Zhao, and Haibo Ge* Table of Contents General Information...
More informationElectronic Supplementary Information
Electronic Supplementary Information A Novel and Facile Zn-mediated Intramolecular Five-membered Cyclization of β-tetraarylporphyrin Radicals from β-bromotetraarylporphyrins Dong-Mei Shen, Chao Liu, Qing-Yun
More informationyellow coloured amorphous powder, which on crystallization from hot acetone resulted in pale
Supporting Information Hexane Extract. Compound I: Elution of column with hexane: dichloromethane (50:50 v/v; 200 ml), gave a pale yellow coloured amorphous powder, which on crystallization from hot acetone
More informationSupporting Information. for. Pd-catalyzed decarboxylative Heck vinylation of. 2-nitro-benzoates in the presence of CuF 2
Supporting Information for Pd-catalyzed decarboxylative Heck vinylation of 2-nitro-benzoates in the presence of CuF 2 Lukas J. Gooßen*, Bettina Zimmermann, Thomas Knauber Address: Department of Chemistry,
More informationSupporting Information. Nitrodibenzofuran: a One- and Two-Photon Sensitive Protecting Group that is Superior to
Supporting Information Nitrodibenzofuran: a One- and Two-Photon Sensitive Protecting Group that is Superior to Brominated Hydroxycoumarin for Thiol Caging in Peptides M. Mohsen Mahmoodi, Daniel Abate-Pella,
More informationSUPPORTING INFORMATION
SUPPORTING INFORMATION Exploiting the Ring Strain in Bicyclo[2.2.1]heptane Systems for the Stereoselective Preparation of Highly Functionalized Cyclopentene, Dihydrofuran, Pyrroline and Pyrrolidine Scaffolds
More informationSensor Enzyme, UDP-Glc: Glycoprotein. Glucosyltransferase
Supporting Information The Recognition Motif of the Glycoprotein-Folding Sensor Enzyme, UDP-Glc: Glycoprotein Glucosyltransferase Kiichiro Totani, * Yoshito Ihara, Takashi Tsujimoto, Ichiro Matsuo, and
More informationSupplementary Material. Efficient Synthesis of an Indinavir Precursor from Biomass Derived (-)- Levoglucosenone
1.171/CH17227_AC CSIRO 217 Australian Journal of Chemistry 217, 7(1), 1146-115 Supplementary Material Efficient Synthesis of an Indinavir Precursor from Biomass Derived (-)- Levoglucosenone Edward T. Ledingham,
More informationSupporting Information
Investigation of self-immolative linkers in the design of hydrogen peroxide metalloprotein inhibitors Jody L. Major Jourden, Kevin B. Daniel, and Seth M. Cohen* Department of Chemistry and Biochemistry,
More informationSupporting Information. for. Access to pyrrolo-pyridines by gold-catalyzed. hydroarylation of pyrroles tethered to terminal alkynes
Supporting Information for Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes Elena Borsini 1, Gianluigi Broggini* 1, Andrea Fasana 1, Chiara Baldassarri
More informationSchwartz s reagent-mediated regiospecific synthesis of 2,3-disubstituted indoles from isatins
Electronic Supplementary Information (ESI) Schwartz s reagent-mediated regiospecific synthesis of 2,3-disubstituted indoles from isatins A. Ulikowski and B. Furman* Institute of Organic Chemistry, Polish
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information ovel pseudo[2]rotaxanes constructed by selfassembly of dibenzyl
More informationCopyright Wiley-VCH Verlag GmbH, D Weinheim, Angew. Chem
Copyright Wiley-VCH Verlag GmbH, D-69451 Weinheim, 2000. Angew. Chem. 2000. Supporting Information for Salen as Chiral Activator : Anti vs Syn Switchable Diastereoselection in the Enantioselective Addition
More informationSupporting Information
Supporting Information De Novo Synthesis of Polysubstituted Naphthols and Furans Using Photoredox Neutral Coupling of Alkynes with 2-Bromo-1,3-Dicarbonyl Compounds Heng Jiang, Yuanzheng Cheng, Yan Zhang,*
More informationThermal shift binding experiments were carried out using Thermofluor 384 ELS system. Protein
Supplementary Methods Thermal shift assays Thermal shift binding experiments were carried out using Thermofluor 384 ELS system. Protein unfolding was examined by monitoring the fluorescence of ANS (1-anilinonaphthalene-8-
More informationSupporting Information. Efficient copper-catalyzed Michael addition of acrylic derivatives with primary alcohols in the presence of base
Supporting Information Efficient copper-catalyzed Michael addition of acrylic derivatives with primary alcohols in the presence of base Feng Wang, a Haijun Yang, b Hua Fu, b,c * and Zhichao Pei a * a College
More informationStructure Elucidation of Verucopeptin, a HIF-1 Inhibitory Polyketide-Hexapeptide Hybrid Metabolite from an Actinomycete.
Structure Elucidation of Verucopeptin, a HIF-1 Inhibitory Polyketide-Hexapeptide Hybrid Metabolite from an Actinomycete. Aya Yoshimura, Shinichi Nishimura, Saori Otsuka, Akira Hattori & Hideaki Kakeya*
More informationEnzymatic resolution and evaluation of enantiomers of. cis-5 -hydroxythalidomide
Electronic Supplementary Information Enzymatic resolution and evaluation of enantiomers of cis-5 -hydroxythalidomide Takeshi Yamamoto, a orio Shibata, a * Masayuki Takashima, a Shuichi akamura, a Takeshi
More informationELECTRONIC SUPPLEMENTARY INFORMATION
ELECTRIC SUPPLEMETARY IFRMATI Searching for new cell-penetrating agents: hybrid cyclobutane-proline γ, γ peptides. Esther Gorrea, a Daniel Carbajo, b,c Raquel Gutiérrez-Abad, a na Illa, a Vicenç Branchadell,
More informationSupporting Information. for. Synthesis of 2,1-benzisoxazole-3(1H)-ones by basemediated. photochemical N O bond-forming
Supporting Information for Synthesis of 2,1-benzisoxazole-3(1H)-ones by basemediated photochemical N O bond-forming cyclization of 2-azidobenzoic acids Daria Yu. Dzhons and Andrei V. Budruev* Address:
More informationScheme S1. Synthesis of glycose-amino ligand.
Scheme S1. Synthesis of glycose-amino ligand. 5-Chloro-1-pentyl-2,3,4,6-tetra-O-acetyl-ß-D-glucopyranoside S2 To a solution of penta-o-acetyl-ß-d-glucopyranoside S1 (3.0 g, 7.69 mmol) and 5-chloropentan-1-ol
More informationSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Supporting Information Facile Three-Step Synthesis and Photophysical Properties of [8]-, [9]-,
More informationSupplementary Materials
Supplementary Materials Supplementary Materials and Methods Biochemical Methods Methods to assay HMT activities have been previously described (1). In vitro cell assays Proliferation and LCC calculations
More informationSupramolecular hydrogels based on bola-amphiphilic glycolipids showing color change in response to glycosidases
Supramolecular hydrogels based on bola-amphiphilic glycolipids showing color change in response to glycosidases Rika Ochi, a Kazuya Kurotani, a Masato Ikeda, c Shigeki Kiyonaka a and Itaru Hamachi* ab
More informationHeparin Sodium ヘパリンナトリウム
Heparin Sodium ヘパリンナトリウム Add the following next to Description: Identification Dissolve 1 mg each of Heparin Sodium and Heparin Sodium Reference Standard for physicochemical test in 1 ml of water, and
More informationElectronic Supplementary Information. Table of Contents
Electronic Supplementary Information Examination of native chemical ligation using peptidyl prolyl thioester Takahiro Nakamura, Akira Shigenaga, Kohei Sato, Yusuke Tsuda, Ken Sakamoto, and Akira Otaka*
More informationSynthesis and Assignment of the Absolute Configuration of an Indenotryptoline Bisindole Alkaloid, BE-54017
Supporting Information Synthesis and Assignment of the Absolute Configuration of an Indenotryptoline Bisindole Alkaloid, BE-54017 Tomoyuki Kimura, Shuhei Kanagaki, Yusuke Matsui, Masaya Imoto, Takumi Watanabe*,,
More information