Naoya Takahashi, Keiya Hirota and Yoshitaka Saga* Supplementary material
|
|
- Rhoda Morrison
- 5 years ago
- Views:
Transcription
1 Supplementary material Facile transformation of the five-membered exocyclic E-ring in demethoxycarbonyl chlorophyll derivatives by molecular oxygen with titanium oxide in the dark Naoya Takahashi, Keiya Hirota and Yoshitaka Saga* Department of Chemistry, Faculty of Science and Engineering, Kinki University, Higashi-Osaka, Osaka , Japan
2 EXPERIMENTAL DETAILS Synthesis Synthesis of methyl pyropheophorbide a (1) Chl a was extracted from Spirulina geitleri with a mixture of methanol and petroleum ether (2/1, vol/vol). Then, 2% HCl was added to the extract solution, and an organic phase was neutralized with aqueous 4% NaHCO 3. The organic phase was washed with distilled water and dried over anhydrous Na 2 SO 4. After evaporation, the residue was dissolved in methanol, followed by addition of a small amount of H 2 SO 4. The solution was stirred overnight under nitrogen in the dark. Then, the reaction mixture was poured into distilled water, and extracted with CH 2 Cl 2. The CH 2 Cl 2 solution was neutralized with saturated NaHCO 3 aq., washed with distilled water, and dried over anhydrous Na 2 SO 4. After evaporation, the residue was dissolved in g-collidine and refluxed for 3.5 h under nitrogen in the dark. After removal of g-collidine under the reduced pressure, the residue was purified by silica-gel flash column chromatography (FCC) and recrystallization to give methyl pyropheophorbide a (1). 1 H NMR (CDCl 3 ): d, ppm 9.40, 9.30, 8.55 (each 1H, s, 5-H, 10-H, 20-H), 7.95 (1H, dd, J=12, 18 Hz, 3-CH), 6.26 (1H, dd, J=1, 18 Hz, 3 1 -CH-trans to 3-CH), 6.15 (1H, dd, J=1, 12 Hz, 3 1 -CH-cis to 3-CH), 5.26, 5.11 (each 1H, d, J=20 Hz, H 2 ), 4.48 (1H, dq, J=2, 8 Hz, 18-H), (1H, m, 17-H), 3.63, , 3.18 (each 3H, s, 2-CH 3, 7-CH 3, 12-CH 3, COOCH 3 ), (2H, m, 8-CH 2 ), , , (1H + 1H + 2H, m, 17- CH 2 CH 2 ), 1.82 (3H, d, J=7 Hz, 18-CH 3 ), 1.66 (3H, t, J=8 Hz, 8 1 -CH 3 ), 0.42, (each 1H, s, NH). 13 C NMR (CDCl 3 ): d, ppm , , , , , , , , , , , , , , , , , , , , 97.08, 92.98, 51.67, 51.63, 49.94, 48.00, 30.91, 29.82, 23.11, 19.38, 17.39, 12.07, 12.00, MS (MALDI): m/z found 548.4, calcd. for C 34 H 36 N 4 O 3 [M] +, UV-vis (CH 2 Cl 2 ): l max, nm 667 (relative intensity, 0.43), 610 (0.08), 539 (0.09), 508 (0.10), 413 (1.00). IR (CH 2 Cl 2 ): n, cm (17 2 -C=O), 1691 (13-C=O), 1621 (C=C). Synthesis of pyropheophytin a (2) Chl a was treated with 2% HCl, followed by neutralization with aqueous 4% NaHCO 3, and dryness over anhydrous Na 2 SO 4. After evaporation, the residue was purified by FCC to give pheophytin a. Pheophytin a was dissolved in g- collidine and refluxed for 3.5 h under nitrogen in the dark. After removal of g-collidine under the reduced pressure, the residue was purified by FCC and recrystallization to give pyropheophytin a (2). 1 H NMR (CDCl 3 ): d, ppm 9.32, 9.22, 8.55 (each 1H, s, 5-H, 10-H, 20-H), 7.91 (1H, dd, J=12, 18 Hz, 3-CH), 6.23 (1H, dd, J=2, 18 Hz, 3 1 -CH-trans to 3-CH), 6.13 (1H, dd, J=2, 12 Hz, 3 1 -CH-cis to 3-CH), 5.28, 5.11 (each 1H, d, J=20 Hz, H 2 ), 5.27 (1H, t, J=7 Hz, P2-H), (2H, m, P1-H 2 ), 4.50 (1H, dq, J=2, 7 Hz, 18-H), 4.30 (1H, dt, J=8, 3 Hz, 17-H), 3.60, 3.39, 3.12 (each 3H, s, 2-CH 3, 7-CH 3, 12-CH 3 ), 3.55 (2H, q, J=8 Hz, 8-CH 2 ), , , (1H + 1H + 2H, m, 17-CH 2 CH 2 ), (2H, m, P4-H 2 ), 1.84 (3H, d, J=7 Hz, 18-CH 3 ), 1.67 (3H, s, P3-CH 3 ), 1.64 (3H, t, J=8 Hz, 8 1 -CH 3 ), (19H, m, P5-H 2, P6-H 2, P7-H, P8-H 2, P9-H 2, P10-H 2, P11-H, P12-H 2, P13-H 2, P14-H 2, P15-H), 0.88, 0.83, 0.81 (6H + 3H + 3H, d, J=7 Hz, P7-CH 3, P11-CH 3, P15-(CH 3 ) 2 ), 0.29, (each 1H, s, NH). MS (MALDI): m/z found 812.1, calcd. for C 53 H 72 N 4 O 3 [M] +, UV-vis (CH 2 Cl 2 ): l max, nm 667 (relative intensity, 0.43), 610 (0.07), 539 (0.09), 508 (0.10), 414 (1.00).
3 Synthesis of Zn pyropheophytin a (3) A methanol solution saturated by Zn acetate was added to an organic solution of 2 and stirred for 2 h under nitrogen in the dark. Aliquot of 4% aqueous NaHCO 3 was added to the reaction solution, and pigments were extracted with diethyl ether. The organic phase was washed with distilled water, and dried over anhydrous Na 2 SO 4. After evaporation, the residue was purified by recrystallization to give Zn pyropheophytin a (3). 1 H NMR (CDCl 3 ): d, ppm 8.70, 8.64, 8.30 (each 1H, s, 5-H, 10-H, 20-H), 7.77 (1H, dd, J=12, 18 Hz, 3-CH), 6.08 (1H, d, J=18 Hz, 3 1 -CH-trans to 3-CH), 5.99 (1H, d, J=12 Hz, 3 1 -CH-cis to 3-CH), 5.07 (1H, t, J=7 Hz, P2-H), 4.46, 4.38 (each 1H, d, J=20 Hz, H 2 ), 4.31 (1H, dq, J=2, 7 Hz, 18-H), (2H, m, P1-H 2 ), 3.99 (1H, d, J=9 Hz, 17-H), 3.28, 3.19, 2.76 (each 3H, s, 2-CH 3, 7-CH 3, 12-CH 3 ), 3.15 (2H, q, J=8 Hz, 8-CH 2 ), , , (2H + 1H + 1H, m, 17-CH 2 CH 2 ), (2H, m, P4-H 2 ), 1.83 (3H, d, J=7 Hz, 18-CH 3 ), 1.56 (3H, s, P3-CH 3 ), (19H, m, P5-H 2, P6-H 2, P7-H, P8-H 2, P9-H 2, P10-H 2, P11-H, P12-H 2, P13-H 2, P14-H 2, P15-H), 1.41 (3H, t, J=8 Hz, 8 1 -CH 3 ), 0.87, 0.82, 0.80 (6H + 3H + 3H, d, J=7 Hz, P7-CH 3, P11-CH 3, P15-(CH 3 ) 2 ). MS (MALDI): m/z found 874.9, calcd. for C 53 H 70 N 4 O 3 Zn [M] +, UV-vis (CH 2 Cl 2 ): l max, nm 655 (relative intensity, 0.71), 606 (0.12), 557 (0.07), 516 (0.05), 424 (1.00). Synthesis of methyl oxo-pyropheophorbide a by LiOH-promoted allomerization LiOH (326 mg) was dissolved in a mixture of distilled water (4.0 ml) and methanol (1.4 ml), and was poured into the THF solution (5 ml) of 1 (52.6 mg). The mixture was stirred vigorously for 3 h in the dark. Then, the reaction mixture was concentrated under reduced pressure and neutralized with acetic acid. The products were extracted with CHCl 3, washed with distilled water, and dried over anhydrous Na 2 SO 4. After evaporation, the residue was dissolved in methanol containing a small amount of H 2 SO 4, and stirred overnight under nitrogen in the dark. The reaction mixture was poured into distilled water, and extracted with CH 2 Cl 2. The CH 2 Cl 2 solution was neutralized with saturated NaHCO 3 aq., washed with distilled water, and dried over anhydrous Na 2 SO 4. After evaporation, the residue was purified by FCC and recrystallization to give methyl oxo-pyropheophorbide a. 1 H NMR (CDCl 3 ): d, ppm 9.77, 9.75, 8.99 (each 1H, s, 5-H, 10-H, 20-H), 8.08 (1H, dd, J=12, 18 Hz, 3-CH), 6.34 (1H, dd, J=1, 18 Hz, 3 1 -CH-trans to 3-CH), 6.26 (1H, d, J=1, 12 Hz, 3 1 -CH-cis to 3-CH), (1H, m, 17-H), 4.69 (1H, q, J=7 Hz, 18-H), 3.80, 3.59, 3.51, 3.29 (each 3H, s, 2-CH 3, 7-CH 3, 12-CH 3, COOCH 3 ), 3.72 (2H, q, J=7 Hz, 8-CH 2 ), , , (1H + 1H + 2H, m, 17-CH 2 CH 2 ), 1.89 (3H, d, J=7 Hz, 18-CH 3 ), 1.71 (3H, t, J=7 Hz, 8 1 -CH 3 ), 0.12, (each 1H, s, NH). 13 C NMR (CDCl 3 ): d, ppm , , , , , , , , , , , , , , , , , , , , , , 95.56, 52.68, 51.61, 49.28, 31.88, 31.51, 23.84, 19.38, 17.44, 12.51, 12.18, HRMS (FAB): m/z found , calcd. for C 34 H 34 N 4 O 4 [M] +, UV-vis (CH 2 Cl 2 ): l max, nm 677 (relative intensity, 0.62), 621 (0.05), 518 (0.14), 421 (0.81), 388 (1.00). IR (CH 2 Cl 2 ): n, cm (17 2 -C=O), 1705 (13-C=O, C=O), 1621 (C=C). Estimation of the conversion efficiencies The conversion efficiencies from 1/2 to 1 /2 by contact with TiO 2 particles in the presence of O 2 was estimated by fitting visible absorption spectra after incubation for 4 h with two Gaussian curves possessing the 667-nm and 677-nm peaks, which were parallel to the Q y absorption bands of 1/2 and 1 /2, respectively. The Q y molar extinction coefficients, e= and M -1 cm -1, for 1/2 [S1] and 1 /2 [S2] were used for estimation of their concentrations. The conversion efficiency from 3 to 3 was estimated in essentially the same manner as in the case of 1
4 and 2 on the hypothesis that the relative ratio of the Q y molecular extintion coefficients of 3 /3 was the same as those of 1 /1. REFERENCES S1. Smith KM, Goff DA, Simpson DJ. J. Am. Chem. Soc., 1985; 107: S2. Ma L, Dolphin D. J. Org. Chem., 1996; 61: 2501.
5 Fig. S1. 1 H NMR spectrum of purified 1 in CDCl 3. denoted CHCl 3 and impurities in the solvent. Fig. S2. 13 C NMR spectrum of purified 1 in CDCl 3. denoted CHCl 3. Fig. S3. 13 C NMR spectra of purified 1 (A), synthesized methyl oxo-pyropheophorbide a (B), and 1 (C) in CDCl 3 between 180 and 200 ppm.
6 Fig. S4. FT-IR spectra of purified 1 (A), methyl oxo-pyropheophorbide a (B), and 1 (C) in CH 2 Cl 2. Fig. S5. FT-IR spectra of purified 1 (A), synthesized methyl oxo-pyropheophorbide a (B), and 1 (C) in CH 2 Cl 2 between 1500 and 1800 cm -1.
7 Fig. S6. On-line visible absorption spectra of major (A: 2 eluted at 86 min) and minor products (B: eluted at 91 min) from 2 by contact with TiO 2 particles in the presence of O 2. Fig. S7. 1 H NMR spectrum of purified 2 in CDCl 3. denoted CHCl 3 and impurities in the solvent.
8 Fig. S8. 13 C NMR spectrum of purified 2 in CDCl 3. denoted CHCl 3. Fig. S9. 1 H NMR spectrum of the purified minor product from 2 in CDCl 3. denoted CHCl 3 and impurities in the solvent.
9 Fig. S10. An on-line visible absorption spectrum of 3 (eluted at 28 min) by contact with TiO 2 particles in the presence of O 2. Fig. S11. 1 H NMR spectrum of purified 3 in CDCl 3. denoted CHCl 3 and impurities in the solvent.
10 Fig. S C NMR spectrum of purified 3 in CDCl 3. denoted CHCl 3.
Electronic 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 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 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 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 informationA pillar[2]arene[3]hydroquinone which can self-assemble to a molecular zipper in the solid state
A pillar[2]arene[3]hydroquinone which can self-assemble to a molecular zipper in the solid state Mingguang Pan, Min Xue* Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China Fax:
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 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 informationChristophe Lincheneau, Bernard Jean-Denis and Thorfinnur Gunnlaugsson* Electronic Supplementary Information
Self-assembly formation of mechanically interlocked [2]- and [3]catenanes using lanthanide ion [Eu(III)] templation and ring closing metathesis reactions Christophe Lincheneau, Bernard Jean-Denis and Thorfinnur
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 informationMasatoshi 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 informationElectronic Supplementary Material
Electronic Supplementary Material PAMAM Dendrimers Bearing Electron-Donating Chromophores: Fluorescence and Electrochemical Properties Bing-BingWang a, Xin Zhang a, Ling Yang a, Xin-Ru Jia* a, Yan Ji a,
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 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. 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 informationSelf-organization of dipyridylcalix[4]pyrrole into a supramolecular cage for dicarboxylates
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information Self-organization of dipyridylcalix[4]pyrrole into a supramolecular
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 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 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 informationSupporting Information
Supporting Information A single design strategy for dual sensitive ph probe with a suitable range to map ph in living cells Kang-Kang Yu, Ji-Ting Hou, Kun Li, * Qian Yao, Jin Yang, Ming-Yu Wu, Yong-Mei
More informationUse of degradable cationic surfactants with cleavable linkages for enhancing the. chemiluminescence of acridinium ester labels. Supplementary Material
Use of degradable cationic surfactants with cleavable linkages for enhancing the chemiluminescence of acridinium ester labels Supplementary Material Anand atrajan*and David Wen Siemens Healthcare Diagnostics
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 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 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 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 informationSupporting Information
Zinc-Mediated Addition of Diethyl Bromomalonate to Alkynes for the Cascade Reaction towards Polysubstituted Pyranones and Tetracarbonyl Derivatives Anne Miersch, Klaus Harms, and Gerhard Hilt* Fachbereich
More informationSupporting information for
Supporting information for A Coordination Gelator that Shows a Reversible Chromatic Change and a Sol-Gel Phase Transition Behavior upon xidative / Reductive Stimuli Shin-ichiro Kawano, orifumi Fujita,
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 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 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 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 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 informationSupporting Information. Copper-catalyzed cascade synthesis of benzimidazoquinazoline derivatives under mild condition
Supporting Information Copper-catalyzed cascade synthesis of benzimidazoquinazoline derivatives under mild condition Shan Xu, Juyou Lu and Hua Fu* Key Laboratory of Bioorganic Phosphorus Chemistry and
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 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 informationAllenylphosphine oxides as simple scaffolds for. phosphinoylindoles and phosphinoylisocoumarins
Supporting Information for Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins G. Gangadhararao, Ramesh Kotikalapudi, M. Nagarjuna Reddy and K. C. Kumara Swamy*
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 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 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 informationmm C3a. 1 mm C3a Time (s) C5a. C3a. Blank. 10 mm Time (s) Time (s)
125 I-C5a (cpm) Fluorescnece Em 520nm a 4000 3000 2000 1000 c 0 5000 4000 3000 2000 Blank C5a C3a 6 0.3 mm C3a 7 9 10 11 12 13 15 16 0.3 mm C5a 0 300 600 900 1200 Time (s) 17 Fluorescnece Em 520nm Fluorescnece
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 informationSupporting Information. Design and Synthesis of Bicyclic Pyrimidinones as Potent and Orally. Bioavailable HIV-1 Integrase Inhibitors.
Supporting Information Design and Synthesis of Bicyclic Pyrimidinones as Potent and Orally Bioavailable HIV-1 Integrase Inhibitors. Ester Muraglia, * Olaf Kinzel, Cristina Gardelli, Benedetta Crescenzi,
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 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. 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 information# Supplementary Material (ESI) for Chemical Communications # This journal is The Royal Society of Chemistry 2005
Electronic Supplementary Information for: (Z)-Selective cross-dimerization of arylacetylenes with silylacetylenes catalyzed by vinylideneruthenium complexes Hiroyuki Katayama,* Hiroshi Yari, Masaki Tanaka,
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. 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. 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 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 informationChemo- and Enantioselective Rh-Catalyzed Hydrogenation of 3-Methylene-1,2-diazetidines: Application to Vicinal Diamine Synthesis
Chemo- and Enantioselective Rh-Catalyzed Hydrogenation of 3-Methylene-1,2-diazetidines: Application to Vicinal Diamine Synthesis Greg P. Iacobini, a David W. Porter, b and Michael Shipman* a a Department
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
Supporting Information for Selectively fluorinated cyclohexane building blocks: Derivatives of carbonylated all-cis-3-phenyl-1,2,4,5- tetrafluorocyclohexane Mohammed Salah Ayoup 1,2, David B. Cordes 1,
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 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 informationOrganic Semiconducting Nanoparticles as Efficient Photoacoustic Agents for Lightening Early Thrombus and
Supporting Information rganic Semiconducting anoparticles as Efficient Photoacoustic Agents for Lightening Early Thrombus and Monitoring Thrombolysis in Living Mice Cao Cui,, Zhen Yang,, Xiang Hu, Jinjun
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 Figure 1. Chemical structures of activity-based probes (ABPs) and of click reagents used in this study.
Supplementary Figure 1. Chemical structures of activity-based probes (ABPs) and of click reagents used in this study. In this study, one fluorophosphonate (FP, 1), three nitrophenol phosphonate probes
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for Chemical Communications. This journal is The Royal Society of Chemistry 2018 Electronic Supplementary Information A ratiometric fluorescence probe for peroxynitrite
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 informationThe oxazoline 6 was prepared according to a literature procedure 2 but on a 30g scale. The 1 H NMR is identical to what was reported.
Supporting Information for: A Facile Approach to 2-Acetamido-2-deoxy-b-D-Glucopyranosides via a Furanosyl xazoline Ye Cai, Chang-Chun Ling and David R. Bundle* Alberta Ingenuity Center for Carbohydrate
More informationAn Unusual Glycosylation Product from a Partially Protected Fucosyl Donor. under Silver Triflate activation conditions. Supporting information
An Unusual Glycosylation Product from a Partially Protected Fucosyl Donor under Silver Triflate activation conditions Robin Daly a and Eoin M. Scanlan* a e-mail: eoin.scanlan@tcd.ie a Trinity Biomedical
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 informationSimple copper/tempo catalyzed aerobic dehydrogenation. of benzylic amines and anilines
Simple copper/tempo catalyzed aerobic dehydrogenation of benzylic amines and anilines Zhenzhong Hu and Francesca M. Kerton,* Department of Chemistry, Memorial University of Newfoundland, St. John s, NL,
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 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 informationDevelopment of a near-infrared fluorescent probe for monitoring hydrazine in serum and living cells
Supporting Information for Development of a near-infrared fluorescent probe for monitoring hydrazine in serum and living cells Sasa Zhu, Weiying Lin,* Lin Yuan State Key Laboratory of Chemo/Biosensing
More informationSupporting Information
Supporting Information Antioxidant Generation and Regeneration in Lipid Bilayers: the Amazing Case of Lipophilic Thiosulfinates and Hydrophilic Thiols Feng Zheng & Derek A. Pratt* Department of Chemistry,
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 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 informationAn Orthogonal Array Optimization of Lipid-like Nanoparticles for. mrna Delivery in Vivo
Supporting Information An rthogonal Array ptimization of Lipid-like Nanoparticles for mrna Delivery in Vivo Bin Li, Xiao Luo, Binbin Deng, Junfeng Wang, David W. McComb, Yimin Shi, Karin M.L. Gaensler,
More informationSupplemental Information. Reactivity of Monovinyl (Meth)Acrylates Containing Cyclic Carbonates
Supplemental Information Reactivity of Monovinyl (Meth)Acrylates Containing Cyclic Carbonates Kathryn A. Berchtold a, Jun Nie b, Jeffrey W. Stansbury c, d, and Christopher N. Bowman c, d, a Materials Science
More informationSupporting Information for. A convenient Method for Epoxidation of Alkenes using Aqueous. Hydrogen Peroxide
Supporting Information for A convenient Method for Epoxidation of Alkenes using Aqueous Hydrogen Peroxide Man Kin Tse, Markus Klawonn, Santosh Bhor, Christian Döbler, Gopinathan Anilkumar, and Matthias
More informationCytosolar delivery of large proteins using nanoparticlestabilized
Electronic Supplementary Material (ESI) for Nanoscale. This journal is The Royal Society of Chemistry 2016 Supporting Information Cytosolar delivery of large proteins using nanoparticlestabilized nanocapsules
More informationIron-Catalyzed Alkylation of Alkenyl Grignard Reagents
Supporting Information for Iron-Catalyzed Alkylation of Alkenyl Grignard Reagents Gérard Cahiez,* Christophe Duplais and Alban Moyeux Laboratoire de Synthèse Organique Sélective et de Chimie Organométallique
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
Supporting Information Synthesis of Pyrido-fused Quinazolinone Derivatives via Copper-catalyzed Domino Reaction Meilin Liu, Miaomiao Shu, Chaochao Yao, Guodong Yin,* Dunjia Wang, and Jinkun Huang* Hubei
More informationSupplementary Information
Supplementary Information Ruthenium(IV) porphyrin catalyzed phosphoramidation of aldehyde with phosphoryl azide as nitrene source Wenbo Xiao, Cong-Ying Zhou and Chi-Ming Che* Department of Chemistry, State
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 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 informationSupporting Information
Supporting Information Developing Activity Localization Fluorescence Peptide Probe Using Thiol-Ene Click Reaction for Spatially Resolved Imaging of Caspase-8 in Live Cells Wei Liu,, Si-Jia Liu,, Yong-Qing
More informationCu-Catalyzed Direct C6-Arylation of Indoles
Cu-Catalyzed Direct C6-Arylation of Indoles (Supporting Information) Youqing Yang, Ruirui Li, Yue Zhao, Dongbing Zhao, and Zhuangzhi Shi*, State Key Laboratory of Coordination Chemistry, Collaborative
More informationPhotoinitiated Multistep Charge Separation in Ferrocene-Zinc Porphyrin- Diiron Hydrogenase Model Complex Triads
upporting Information for Photoinitiated Multistep Charge eparation in rrocene-zinc Porphyrin- Diiron Hydrogenase Model Complex Triads Premaladha Poddutoori, Dick T. Co, Amanda P.. amuel, Chul Hoon Kim,
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. 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 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 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 Conformationally Induced Off-On Cell Membrane Chemosensor Targeting Receptor Protein-Tyrosine Kinases for in Vivo and in Vitro Fluorescence Imaging of Cancers Yang Jiao,, Jiqiu Yin,
More informationNHC-catalyzed cleavage of vicinal diketones and. triketones followed by insertion of enones and
Supporting Information for NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones Ken Takaki*, Makoto Hino, Akira Ohno, Kimihiro Komeyama, Hiroto Yoshida
More informationPt IV azido complexes undergo copper-free click reactions with alkynes
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 208 Pt IV azido complexes undergo copper-free click reactions with alkynes Electronic Supplementary
More informationElectronic Supporting Information
Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers. This journal is the Partner Organisations 2018 Electronic Supporting Information Tetraphenylpyrazine-based luminogens with full-colour
More informationDual-site Controlled and Lysosome-targeted ICT-PET-FRET. Fluorescent Probe for Monitoring ph Changes in Living Cells
Supporting information for Dual-site Controlled and Lysosome-targeted ICT-PET-FRET Fluorescent Probe for Monitoring ph Changes in Living Cells Baoli Dong, Xuezhen Song, Chao Wang, Xiuqi Kong, Yonghe Tang
More informationAcyl Radical Reactions in Fullerene Chemistry: Direct Acylation of. [60]Fullerene through an Efficient Decatungstate-Photomediated Approach.
Supporting information Acyl Radical Reactions in Fullerene Chemistry: Direct Acylation of [60]Fullerene through an Efficient Decatungstate-Photomediated Approach. Manolis D. Tzirakis and Michael rfanopoulos
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 informationin palmitoylation of numerous proteins. P10 mitochondria enriched fractions from primary rat
SUPPLEMENTARY MATERIALS: Supplementary Figures: Supplementary Figure S1. Alkynyl-palmitate is readily imported into mitochondria resulting in palmitoylation of numerous proteins. P10 mitochondria enriched
More informationHetero Bodipy-dimers as heavy atom-free triplet photosensitizer showing long-lived triplet excited state for triplet-triplet annihilation upconversion
Electronic Supplementary Information for: Hetero odipy-dimers as heavy atom-free triplet photosensitizer showing long-lived triplet excited state for triplet-triplet annihilation upconversion Wanhua Wu,
More informationEasily removable olefin metathesis catalysts
Easily removable olefin metathesis catalysts Krzysztof Skowerski,*a Celina Wierzbicka,a Grzegorz Szczepaniak,b Łukasz Gułajski, a Michał Bieniek, a and Karol Grela*b a Apeiron Synthesis Sp. z o.o., Klecińska
More informationSupplementary Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Supplementary Information Oxidative Tandem Annulation of 1 (2 Ethynylaryl)prop 2 en 1 ones Catalyzed
More informationUniversity of Groningen
University of Groningen Copper phosphoramidite-catalyzed enantioselective desymmetrization of meso-cyclic allylic bisdiethyl phosphates Piarulli, Umberto; Claverie, Christelle; Daubos, Philippe; Gennari,
More informationRuthenium-Catalyzed C H Oxygenation on Aryl Weinreb Amides
Supporting Information Ruthenium-Catalyzed C H xygenation on Aryl Weinreb Amides Fanzhi Yang and Lutz Ackermann* Institut für rganische und Biomolekulare Chemie Georg-August-Universität Tammannstrasse
More information