Microwave heating in peptide side chain modification via sulfhydryl reaction
|
|
- Sibyl Skinner
- 6 years ago
- Views:
Transcription
1 Microwave heating in peptide side chain modification via sulfhydryl reaction E. Calce and S. De Luca* Institute of Biostructures and Bioimaging, National Research Council, Naples, Italy Electronic Supplementary Information Table of contents 1. Experimental section S2 2. LC-MS spectra of pure modified peptides S6 3. MW parameters S11 4. NMR spectra of modified peptides S13
2 1. Experimental section 1.1 Materials Fmoc protected amino acids, Rink Amide MBHA resins (0.7 mmol g -1 ), NovaSyn TGA resin (0.2 mmol g -1 ), N-hydroxybenzotriazole (HOBT), benzotriazol-1-yl-oxy-tris-pyrrolidino-phosphonium (PyBOP) were purchased from Calbiochem-Novabiochem (Laufelfingen, Switzerland); piperidine and diisopropylethylamine (DIPEA) were purchased from Fluka (Milwaukee, WI), all remaining solvents were purchased from Sigma-Aldrich (St Louis, MO) or Fluka (Milwaukee, WI) and were used without further purification, unless otherwise stated. Molecular sieves type 4 Å (beads, diameter 1.6 mm), Fmoc-L-Cys(Mmt)-OH and all remaining alkyl bromides were purchased from Sigma-Aldrich. 1.2 General procedure for the MW-assisted peptide S-alkylation AcGlyCys(Bn)ValAlaNH 2 (1a). HPLC: t R = 5.27 min; ES-MS: calculated [M + H] +, 480.2, found m/z H NMR (400 MHz, DMSO), 1.90 (acetyl CH 3 ); 8.17, 3.77 (Gly H N, H -H '); Cys H N, H, H -H '), 7.36, 7.30, 3.80 (Bn); 8.09, 4.20, 2.07, 0.91 (Val H N, H, H, H ); 7.90, 4.24, 1.22, (Ala H N, H, H, CONH 2 ). AcAspGlyCys(Bn)ValAlaNH 2 (2a). Peptide 2a was synthesized, characterized and purified under the experimental conditions described for 1a. The benzyl bromide was employed as alkylating agent (2.1 µl, mmol). The final RP-HPLC purification provided compound 2a in 52% yield (5.2 mg). HPLC: t R = 4.33 min; ES-MS: calculated [M + H] +, 595.3, found m/z H NMR (400 MHz, DMSO), 1.89 (acetyl CH 3 ); 8.27, 4.57, (Asp H N, H, H -H '); 8.18, 3.76 (Gly H N, H -H '); Cys H N, H, H -H '),, 7.36, 7.28, 3.80 (Bn); 8.08, 4.18, 2.07, 0.90 (Val H N, H, H, H ); 7.92, 4.24, 1.21, (Ala H N, H, H, CONH 2 ). AcArgGlyCys(Bn)ValAlaNH 2 (3a). Peptide 3a was synthesized, characterized and purified under the experimental conditions described for 1a. The benzyl bromide was employed as alkylating agent (1.9 µl, mmol). The final RP-HPLC purification provided compound 3a in 49% yield (4.9 mg). HPLC: t R = 5.16 min; ES-MS: calculated [M + H] +, 636.3, found m/z H NMR (400 MHz, DMSO), 1.90 (acetyl CH 3 ); 8.16, 4.30, , 1.56, 3.14, 7.50 (Arg H N, H, H -H ', H, H ); 8.29, 3.78 (Gly H N, H -H '); Cys H N, H, H - S2
3 H '), 7.37, 7.29, 3.80 (Bn); 8.09, 4.21, 2.07, 0.90 (Val H N, H, H, H ); 7.93, 4.24, 1.22, (Ala H N, H, H, CONH 2 ). AcHisGlyCys(Bn)ValAlaNH 2 (4a). Peptide 4a was synthesized, characterized and purified under the experimental conditions described for 1a. The benzyl bromide was employed as alkylating agent (2.0 µl, mmol). The final RP-HPLC purification provided compound 4a in 53% yield (5.3 mg). HPLC: t R = 4.30 min; ES-MS: calculated [M + H] +, 617.3, found m/z H NMR (400 MHz, DMSO), 1.89 (acetyl CH 3 ); 8.23, 4.64, , 7.43, 8.99 (His H N, H H - H ', H ); 8.33, 3.84 (Gly H N, H -H '); Cys H N, H, H -H '), 7.36, 7.28, 3.81 (Bn); 8.13, 4.22, 2.07, 0.90 (Val H N, H, H, H ); 7.94, 4.24, 1.22, (Ala H N, H, H, CONH 2 ). AcTrpGlyCys(Bn)ValAlaNH 2 (5a). Peptide 5a was synthesized, characterized and purified under the experimental conditions described for 1a. The benzyl bromide was employed as alkylating agent (1.8 µl, mmol). The final RP-HPLC purification provided compound 5a in 55% yield (5.5 mg). HPLC: t R = 6.65 min; ES-MS: calculated [M + H] +, 666.7, found m/z H NMR (400 MHz, DMSO), 1.81 (acetyl CH 3 ); 8.16, 4.53, , 7.19, 10.81, 7.01, 7.63, 7.10, 7.37 (Trp H N, H, H -H ', H H 1, H H 3, H 2, H ; 8.39, 3.77 (Gly H N, H -H '); Cys H N, H, H -H '), 7.36, 7.29, 3.81 (Bn); 8.10, 4.20, 2.07, 0.91 (Val H N, H, H, H ); 7.91, 4.24, 1.21, (Ala H N, H, H, CONH 2 ). AcLysGlyCys(Bn)ValAlaNH 2 (6a). Peptide 6a was synthesized, characterized and purified under the experimental conditions described for 1a. The benzyl bromide was employed as alkylating agent (2.1 µl, mmol). The final RP-HPLC purification provided compound 6a in 45% yield (4.5 mg). HPLC: t R = 4.19 min; ES-MS: calculated [M + H] +, 608.3, found m/z H NMR (400 MHz, DMSO) 1.90 (acetyl CH 3 ); 8.11, 4.27, , 1.36, 1.55, 2.81, 7.66 (Lys H N, H, H -H ', H H, H, H ; 8.25, 3.76 (Gly H N, H -H '); Cys H N, H, H -H '); 7.37, 7.29, 3.81 (Bn); 8.09, 4.21, 2.07, 0.90 (Val H N, H, H, H ); 7.92, 4.23, 1.22, (Ala H N, H, H, CONH 2 ). AcGlyTrpCys(Dpm)HisValAlaNH 2 (7b). Peptide 7b was synthesized under the experimental conditions described for 1a. Concerning the alkylation, 1-bromo-2-methylnaphthalene (4.2 mg, mmol) was employed as alkylating agent, and the solution was irradiated for 15 min at 40 C in a microwave oven. Then, the mixture was centrifuged in order to eliminate the sieves and the S3
4 supernatant was concentrated under vacuum. RP-HPLC and mass spectrometry analysis were carried out by using linear gradient from 20 to 90% B in 30 min and from 20 to 90% B in 10 min, respectively. The final RP-HPLC purification provided compound 7b in 55% yield (5.5 mg), as estimated after lyophilization. HPLC: t R = 3.79 min; ES-MS: calculated [M + H] +, 879.5, found m/z H NMR (400 MHz, DMSO) 1.86 (acetyl CH 3 ); 8.13, , (Gly H N, H -H '); 8.08, 4.62, , 7.17, 10.86, 7.01, 7.61, 7.10, 7.35 (Trp H N, H, H -H ', H H 1, H H 3, H 2, H Cys H N, H, H -H '), , 5.42 (Dpm) ; 8.39, 4.72, , 7.42, 8.94 (His H N, H, H -H ', H H 1); 7.88, 4.19, 2.02, 0.85 (Val H N, H, H, H ); 8.14, 4.26, 1.26, (Ala H N, H, H, CONH 2 ). AcGlyTrpCys(Far)HisValAlaNH 2 (7c). Peptide 7c was synthesized, characterized and purified under the experimental conditions above described for peptide 7b. The trans, trans farnesyl bromide (4.6 µl, mmol) was employed as alkylating agent. The final RP-HPLC purification provided compound 7c in 50% yield (5.0 mg), as estimated after lyophilization. HPLC: t R = 8.66 min; ES-MS: calculated [M + H] +, 917.6, found m/z H NMR (400 MHz, DMSO) 1.85 (acetyl CH 3 ); 8.13, , (Gly H N, H -H '); 8.08, 4.59, , 7.19, 10.86, 7.02, 7.62, 7.09, 7.37 (Trp H N, H, H -H ', H H 1, H H 3, H 2, H Cys H N, H, H -H '), 5.23, 5.13, 5.11, 3.21, 2.08, 2.03, 1.97, 1.68, 1.67, 1.60 (farnesyl); 8.32, 4.72, , 7.36, 8.98 (His H N, H, H -H ', H H 1); 7.85, 4.21, 2.08, 0.90 (Val H N, H, H, H ); 8.14, 4.26, 1.27, (Ala H N, H, H, CONH 2 ). AcGlyTrpCys(HD)HisValAlaNH 2 (7d). Peptide 7d was synthesized, characterized and purified under the experimental conditions above described for peptide 7b. The hexadecyl bromide was employed as alkylating agent (5.2 µl, mmol). The final RP-HPLC purification provided compound 7d in 42% yield (4.2 mg). HPLC: t R = 8.32 min; ES-MS: calculated [M + H] +, 937.7, found m/z H NMR (400 MHz, DMSO) 1.86 (acetyl CH3); 8.13, (Gly H N, H -H ',); 8.07, 4.58, , 7.18, 10.86, 7.02, 7.62, 7.10, 7.37 (Trp H N, H, H -H ', H, H 1, H 3 H 3, H 2, H , 4.41, (Cys H N, H, H -H '), 2.55, 1.53, 1.36, 1.29, 0.90 (HD); 8.38, 4.72, , 7.38, 8.93 (His H N, H, H -H ', H 2, H 1); 7.82, 4.20, 2.06, 0.91 (Val H N, H, H, H ); 8.14, 4.26, 1.26, (Ala H N,+ H, H, CONH 2 ). 1.3 General procedure for the MW-assisted peptide solid-phase S-alkylation S4
5 For the synthesis of compound 1, appropriate Fmoc-amino acid derivatives [Fmoc-Gly-OH, Fmoc- Cys(Mmt)-OH, Fmoc-Val-OH, Fmoc-Ala-OH] were employed and the Rink Amide MBHA resin (0.7 mmol g -1 substitution; 50 µmol scale) was used as solid support. The removal of the Mmt group was performed by washing the peptidyl-resin with TFA-TIS-CH 2 Cl 2 (1:5:94) (10 3 min) and then with CH 2 Cl 2 (5 1 min). Then, the peptidyl resin, acetylated at the N-terminus, was placed in a ml microwave vial, and suspended in ~3 ml of DMF under argon atmosphere. Subsequently, benzyl bromide (5 equiv) was added by a syringe and, as final step, 4 Å molecular sieves (3-3.5 g), previously activated at 280 C for 4 h under vacuum (10-4 mbar), cooled at r.t., were quickly added. The mixture was irradiated for 5-15 min at 40 C in a microwave oven and stirred at 320 rpm. Afterwards, the peptidyl-resin, suspended in abundant DMF, was firstly isolated from the molecular sieves and, then, from the reaction mixture by filtration. After cleavage procedure, the crude product was isolated by precipitation in cold diethyl ether, purified by preparative RP-HPLC, analyzed and characterized by mass spectrometry. S5
6 2. LC-MS spectra of pure modified peptides AcGlyCys(Bn)ValAlaNH 2 (1a) AcAspGlyCys(Bn)ValAlaNH 2 (2a) S6
7 AcArgGlyCys(Bn)ValAlaNH 2 (3a) AcHisGlyCys(Bn)ValAlaNH 2 (4a) S7
8 AcTrpGlyCys(Bn)ValAlaNH 2 (5a) AcLysGlyCys(Bn)ValAlaNH 2 (6a) S8
9 AcGlyTrpCys(Dpm)HisValAlaNH 2 (7b) AcGlyTrpCys(Far)HisValAlaNH 2 (7c) S9
10 AcGlyTrpCys(HD)HisValAlaNH 2 (7d) S10
11 3. MW parameters AcGlyCys(Bn)ValAlaNH 2 (1a) Status: OK Absorption level: Normal Vial type: ml Pre-stirring: 0 Initial power: 0 Dynamic deflector optimization: On Temperature ( C) Pressure (bar) Power (W) S11
12 AcGlyTrpCys(Dpm)HisValAlaNH 2 (7b) Status: OK Absorption level: Normal Vial type: ml Pre-stirring: 0 Initial power: 0 Dynamic deflector optimization: On Temperature ( C) Pressure (bar) Power (W) S12
13 4. NMR spectra of modified peptides , ; ; ; ; 8.17; S13
14 ; 2.79; 2.69; ; ; ; ; ; 8.18; 8.08; 8.07 S14
15 ; ; ; 4.24; ; ; 8.16; 8.14; 8.09 S15
16 ; ; ; ; ; ; 7.36; ; 8.26; 8.23; S16
17 ; ; ; ; ; ; 7.36; 7.29; 7.26; 7.19; 7.10; 7.03; ; 8.16; S17
18 ; 1.55; ; 2.79; ; ; 4.23; ; ; 8.11; 8.10; 8.09 S18
19 ; ; 3.12; 3.04; ; ; ; 4.62; ; 7.42; 7.35; 7.28; 7.26; 7.17; 7.10; 7.01; ; 8.33; 8.14; 8.13; S19
20 ; 1.67; ; 2.03; ; 3.19; 3.13; 3.01; 2.99; 2.82; ; ; 4.59; 4.44; 4.26; ; 5.13; ; 7.36; 7.29; 7.19; 7.09; ; 8.14; 8.13; S20
21 1.30; 1.29; ; ; 3.12; 3.04; 2.98; 2.85; 2.73; ; ; 4.58; 4.41; 4.26; ; 7.37; 7.29; 7.18; 7.10; 7.02; ; 8.27; 8.14; 8.13; S21
Toxins 2016, 8, 222; doi: /toxins
S1 of S8 Supplementary Materials: Mapping Protein Protein Interactions of the Resistance Related Bacterial Zeta Toxin Epsilon Antitoxin Complex (ε2ζ2) with High Affinity Peptide Ligands Using Fluorescence
More informationAutomated synthesis of backbone protected peptides
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information Automated synthesis of backbone protected peptides Abu-Baker
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 informationSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Chemoselective Peptide Cyclization via Induced Traceless Staudinger Ligation Rolf Kleineweischede, Christian P.R. Hackenberger* Institute for
More informationRose et al. Supplementary Material. 1. Supplementary Materials and Methods
Rose et al. Supplementary Material 1. Supplementary Materials and Methods 1.1. Synthesis of the biotinylated CrA modules. 1.1.1. Instrumentation and reagents: All solvents were purchased from Carl Roth
More informationElectronic Supplementary Information
Electronic Supplementary Information PHIP-Label: Parahydrogen-Induced Polarization in Propargylglycine-Containing Synthetic Oligopeptides Marco Körner, Grit Sauer, Andreas Heil, Daichi Nasu, Daniel Tietze,
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 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 informationSupporting Information
Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany Free Radical Based, Specific Desulfurization of Cysteine: A Powerful Advance in the Synthesis of Polypeptides and Glycopolypeptides Qian Wan
More informationAn efficient methodology to introduce o-(aminomethyl) phenyl-boronic acids into peptides: alkylation of secondary amines
Electronic Supplementary Material (ESI) for ew Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre ational de la Recherche Scientifique 2016 An efficient methodology to
More informationSupporting Information
Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany A Convergent Synthesis of N-Linked Glycopeptides Clyde M. Kaneshiro, Katja Michael* 1. LC-MS analysis of crude glycopeptide 16. 2. ESI-TOF
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 informationDevelopment of a Cell-penetrating Peptide that Exhibits Responsive. Changes in its Secondary Structure in the Cellular Environment
Development of a Cell-penetrating Peptide that Exhibits Responsive Changes in its Secondary Structure in the Cellular Environment iroko Yamashita, 1 Takuma Kato, 2 Makoto ba, 2 Takashi Misawa, 1 Takayuki
More informationA Stable Evans Blue Derived Exendin-4 peptide for Type 2 Diabetes Treatment
Supporting Information A Stable Evans Blue Derived Exendin-4 peptide for Type 2 Diabetes Treatment Yi Liu, Guohao Wang, Huimin Zhang, Ying Ma, Lixin Lang, Orit Jacobson, Dale O. Kiesewetter, Lei Zhu, Shi
More informationSupplementary Information
Supplementary Information Efficient use of the Dmab Protecting Group: Applications for the Solid-Phase Synthesis of N- Linked Glycopeptides Trent Conroy, Katrina A. Jolliffe and Richard J. Payne* School
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 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 TO: Oligonucleotide cyclization: The thiol-maleimide reaction revisited. Albert Sánchez, Enrique Pedroso, Anna Grandas*
SUPPRTIG IFRMATI T: ligonucleotide cyclization: The thiol-maleimide reaction revisited. Albert Sánchez, Enrique Pedroso, Anna Grandas* 1. General materials and methods, and abbreviations. 2. Solid phase
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 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 informationAn intermolecular binding mechanism involving multiple LysM domains mediates carbohydrate recognition by an endopeptidase
Supporting information Volume 71 (2015) Supporting information for article: An intermolecular binding mechanism involving multiple LysM domains mediates carbohydrate recognition by an endopeptidase Jaslyn
More informationXu Yang 1, Vasily Gelfanov 2, Fa Liu 2 * and Richard DiMarchi 1,2 *
Supporting Information A New Synthetic Route to Human Relaxin-2 Xu Yang 1, Vasily Gelfanov 2, Fa Liu 2 * and Richard DiMarchi 1,2 * 1 Department of Chemistry, Indiana University, Bloomington, Indiana,
More informationCarboMAX TM Enhanced Peptide Coupling at Elevated Temperature
Page 1 of 5 CarboMAX TM Enhanced Peptide Coupling at Elevated Temperature Summary CarboMAX is a new patented coupling methodology for peptide synthesis at elevated temperature. It offers improvements over
More informationSUPPLEMENTARY RESULTS 2 EXPERIMENTAL METHODS 5 REAGENTS AND EQUIPMENT 5 SYNTHESIS OF 1,3,5-TRIS(MERCAPTOMETHYL)BENZENE (2) 5 SYNTHESIS OF
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 SUPPLEMENTARY RESULTS 2 EXPERIMENTAL METHODS 5 REAGENTS AND EQUIPMENT 5 SYNTHESIS OF 1,3,5-TRIS(MERCAPTOMETHYL)BENZENE
More informationNature Biotechnology: doi: /nbt.2354
a b c Summed up peptide ion signals (arb. u.) 1E+03 INSR 1E+02 1E+01 1E+00-10 - 5 0 5 10 Summed up peptide ion signals (arb. u.) 1E+03 INSR 1E+02 1E+01 1E+00-10 -5 0 5 10 1E+03 1E+02 1E+01 INSR 1E+00-10
More informationSupplemental Information
Electronic upplementary Material (EI) for rganic & Biomolecular Chemistry. This journal is The Royal ociety of Chemistry 2014 upplemental Information olid-phase ynthesis of Peptoid-like ligomers Containing
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 informationEnabling N-to-C Ser/Thr Ligation for Convergent Protein Synthesis via Combining Chemical Ligation Approaches. Supplementary Information
Enabling N-to-C Ser/Thr Ligation for Convergent Protein Synthesis via Combining Chemical Ligation Approaches Chi Lung Lee, Han Liu, Clarence T. T. Wong, Hoi Yee Chow and Xuechen Li* Department of Chemistry,
More informationSupporting Information
Supporting Information Visible-Light-Induced Specific Desulfurization of Cysteinyl Peptide and Glycopeptide in Aqueous Solution Xiao-Fei Gao, Jing-Jing Du, Zheng Liu and Jun Guo* Key Laboratory of Pesticide
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 informationSupporting Information
Supporting Information Cyclic Peptidyl Inhibitors against Human Peptidyl-Prolyl Isomerase Pin1 Tao Liu, Yu Liu, Hung-Ying Kao, *,, and Dehua Pei Table of Contents: Table S1. Structures of amino acid building
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 informationStudy of On-Resin Convergent Synthesis of N-Linked. Glycopeptides Containing a Large High Mannose N- Linked Oligosaccharide
Supporting Information Study of On-Resin Convergent Synthesis of N-Linked Glycopeptides Containing a Large High Mannose N- Linked Oligosaccharide Rui Chen and Thomas J. Tolbert* Department of Chemistry,
More informationEfficient and green, microwave assisted synthesis of haloalkylphosphonates via Michaelis-Arbuzov reaction
ELECTRONIC SUPPORTING INFORMATION Efficient and green, microwave assisted synthesis of haloalkylphosphonates via Michaelis-Arbuzov reaction Petr Jansa, Antonín Holý, Martin Dračinský, Ondřej Baszczyňski,
More informationSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007 Supporting Information General. NMR spectra for identification of intermediates and final compoundswere recorded
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 informationTriptycene-Based Small Molecules Modulate (CAG) (CTG) Repeat Junctions
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2015 Triptycene-Based Small Molecules Modulate (CAG) (CTG) Repeat Junctions Stephanie A. Barros
More informationSupporting Information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information 1. General Information...S2 a. Materials b. HPLC
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 informationSupplementary Information: Click-click chemistry on a peptidic scaffold for the easy access to tetrameric DNA structures
Supplementary Information: Click-click chemistry on a peptidic scaffold for the easy access to tetrameric DNA structures Romaric Bonnet, a Pierre Murat, a Nicolas Spinelli, a and Eric Defrancq* a a Département
More informationPhotocontrolled Interconversion of Cationic and Radical Polymerizations
Photocontrolled Interconversion of Cationic and Radical Polymerizations Veronika Kottisch, Quentin Michaudel, and Brett P. Fors* Cornell University, Ithaca, New York, 14853, United States Supporting Information
More informationIn situ thioester formation for protein ligation using α-methyl cysteine F. Burlina, G. Papageorgiou, Caroline Morris, Peter D. White and J.
Electronic Supplementary Information In situ thioester formation for protein ligation using α-methyl cysteine F. Burlina, G. Papageorgiou, Caroline Morris, Peter D. White and J. Offer* Abbreviations ACN:
More informationTEPZZ 757_Z7A_T EP A1 (19) (11) EP A1. (12) EUROPEAN PATENT APPLICATION published in accordance with Art.
(19) TEPZZ 77_Z7A_T (11) EP 2 77 7 A1 (12) EUROPEAN PATENT APPLICATION published in accordance with Art. 3(4) EPC (43) Date of publication: 23.07.14 Bulletin 14/ (21) Application number: 12831927.4 (22)
More informationTotal chemical synthesis of proteins without HPLC purification
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2016 Supporting Information Total chemical synthesis of proteins without HPLC purification Simon
More informationSUPPLEMENTARY INFORMATION
Internal Dynamics of a Supramolecular Nanofiber Julia H. Ortony 1, Christina Newcomb 1,2, John B. Matson 1, Liam C. Palmer 3, Peter E. Doan 3, Brian M. Hoffman 3, and Samuel I. Stupp 1,2,3,4 1 Institute
More informationElectronic Supplementary Information. Multivalency: Influence of the Residence Time and the Retraction Rate on. Rupture Forces Measured by AFM
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information Multivalency: Influence of the Residence
More informationSynthesis and Conformational Study of Water-Soluble, Rigid, Rod-like Oligopiperidines
Synthesis and Conformational Study of Water-Soluble, Rigid, Rod-like Oligopiperidines Vincent Semetey, Demetri Moustakas and George M. Whitesides* Department of Chemistry and Chemical Biology, Harvard
More informationCytosolic targeting of macromolecules using a ph-dependent fusogenic peptide in. combination with cationic liposomes
Cytosolic targeting of macromolecules using a ph-dependent fusogenic peptide in combination with cationic liposomes Sachiko Kobayashi, Ikuhiko Nakase, Noriko Kawabata, Hao-hsin Yu, Silvia Pujals, Miki
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 informationSUPPLEMENTAL FIGURE 1 Structures and IC50 values of compounds 13 32
SUPPLEMETAL FIGURE 1 Structures and IC50 values of compounds 13 32 THE JURAL F UCLEAR MEDICIE Vol. 53 o. 11 ovember 2012 Synthesis of [ 19 F]1 ([ 19 F]--(2-{4-[5-(benzyloxy)pyridin-2-yl]piperazin-1-yl}-2-oxoethyl)-
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 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 informationYnamides as racemization-free coupling reagents for amide and peptide synthesis
Ynamides as racemization-free coupling reagents for amide and peptide synthesis Long Hu, Silin Xu, Zhenguang Zhao, Yang Yang, Zhiyuan Peng, Ming Yang, Changliu Wang, Junfeng Zhao* Key Laboratory of Chemical
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 informationSupplementary Information for. A facile N-mercaptoethoxyglycinamide (MEGA) linker approach to peptide thioesterification and cyclization
Supplementary Information for A facile N-mercaptoethoxyglycinamide (MEGA) linker approach to peptide thioesterification and cyclization Patrick M. M. Shelton, Caroline E. Weller, and Champak Chatterjee
More informationSupporting Information
Supporting Information Asymmetric Catalysis of the Carbonyl-Amine Condensation: Kinetic Resolution of Primary Amines Sayantani Das, Nilanjana Majumdar, Chandra Kanta De, Dipti Sankar Kundu, Arno Döhring,
More informationAcid-Labile Cys-Protecting Groups for the Fmoc/tBu Strategy: Filling the Gap
Acid-Labile Cys-Protecting Groups for the Fmoc/tBu Strategy: Filling the Gap Miriam Góngora-Benítez,, Lorena Mendive-Tapia,, Iván Ramos-Tomillero,, Arjen C. Breman, Judit Tulla-Puche*,, and Fernando Albericio*,,,,
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Electronic Supplementary Information A Catalytic ne-step Synthesis of Peptide Thioacids: The Synthesis
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 informationSupporting Information. Zinc hydroxide nanostrands: unique precursor for ZIF-8. thin membranes toward highly size-sieving gas separation
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Zinc hydroxide nanostrands: unique precursor for ZIF-8 thin membranes
More informationSynthesis of Human GLP-1 (7-36) by Chemoselective α-ketoacid Hydroxylamine Peptide Ligation of Unprotected Fragments
Synthesis of uman GLP-1 (7-36) by Chemoselective α-ketoacid ydroxylamine Peptide Ligation of Unprotected Fragments Jian Wu a, Javier Ruiz- Rodríguez c, Jeanne M. Comstock, b Jesse Z. Dong b and Jeffrey
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 informationSupplementary Material
10.1071/C15460_AC CSIR 2016 Australian Journal of Chemistry 69 (3), 328-335 Supplementary Material Synthesis and Characterization of Bradykinin Derivatives Based on a β-cyclodextrin Core Rachel J. Stephenson,
More informationTITLE: Development of a Tetrathioether (S4) Bifunctional Chelate System for Rh-105
AD Award Number: W81XWH-11-1-0406 TITLE: Development of a Tetrathioether (S4) Bifunctional Chelate System for Rh-105 PRINCIPAL INVESTIGATOR: Valerie Carroll CONTRACTING ORGANIZATION: University of Missouri,
More informationEvaluation of Chemical Labeling Strategies for Monitoring HCV RNA using Vibrational Microscopy
Electronic Supplementary Information Evaluation of Chemical Labeling Strategies for Monitoring HCV RA using Vibrational Microscopy Matthew oestheden 1,2, Qingyan Hu 1, Angela M. Tonary 1, Li-Lin Tay 3,
More informationAll chemicals were obtained from Aldrich, Acros, Fisher, or Fluka and were used without
Supplemental Data Alexander et al. Experimental Procedures General Methods for Inhibitor Synthesis All chemicals were obtained from Aldrich, Acros, Fisher, or Fluka and were used without further purification,
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 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 informationSpecific N-Alkylation of Hydroxypyridines Achieved by a Catalyst- and Base-Free Reaction with Organohalides
Supporting Information Specific N-Alkylation of Hydroxypyridines Achieved by a Catalyst- and Base-Free Reaction with Organohalides Bin Feng, Yang Li, Huan Li, Xu Zhang, Huamei Xie, Hongen Cao, Lei Yu,
More informationSite-specific traceless coupling of potent cytotoxic drugs to recombinant antibodies for pharmacodelivery.
S1 Site-specific traceless coupling of potent cytotoxic drugs to recombinant antibodies for pharmacodelivery. Giulio Casi, Nicolas Huguenin-Dezot, Kathrin Zuberbühler, Jörg Scheuermann & Dario Neri,* Philochem
More informationSupporting Information
Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany Auxiliary mediated site-specific peptide ubiquitylation Champak Chatterjee, Robert K. McGinty, Jean-Philippe Pellois, and Tom W. Muir * Laboratory
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 informationSupplementary Notes. HTS compatible FRET-based conformational sensors clarify membrane receptor activation
Supplementary otes TS compatible FRET-based conformational sensors clarify membrane receptor activation Pauline Scholler 1,2,3,4, David Moreno-Delgado 1,2,3, athalie Guillet-Lecat 1,2,3, Etienne Doumazane
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: Daniel Knappe, Stefania Piantavigna, Anne Hansen, Adam Mechler, Annegret Binas,
Supporting Information for: Oncocin (VDKPPYLPRPRPPRRIYNR-NH 2 ): a novel antibacterial peptide optimized against Gram-negative human pathogens Daniel Knappe, Stefania Piantavigna, Anne Hansen, Adam Mechler,
More informationSupporting Information
Translation of DNA into Synthetic N-Acyloxazolidines Xiaoyu Li, Zev. J. Gartner, Brian N. Tse and David R. Liu* Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts
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
Supporting Information Wiley-VCH 2013 69451 Weinheim, Germany Construction of a Photoactivated Insulin Depot** Piyush K. Jain, Dipu Karunakaran, and Simon H. Friedman* anie_201207264_sm_miscellaneous_information.pdf
More informationUniChemo Protection: A Novel Concept For Chemical Synthesis. Les P. Miranda and Morten Meldal
Copyright WILEY-VCH Verlag GmbH, D-69451 Weinheim, 2001. Supporting Information for Angew. Chem. Int. Ed. Z17269 UniChemo Protection: A ovel Concept For Chemical Synthesis Les P. Miranda and Morten Meldal
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 informationSupplementary Material (ESI) for Journal of Materials Chemistry This journal is The Royal Society of Chemistry 2006
Electronic Supplementary Information (ESI) for Manuscript: Org. Biomol. Chem. (Title: Development of a linear type of low molecular weight CXCR4 antagonists based on T140 analogs) Experimental Genaral
More informationSelenazolidine: a selenium containing proline surrogate in peptide science.
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Materials lenazolidine: a selenium containing proline
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
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 informationDirect ortho-c H Functionalization of Aromatic Alcohols Masked by Acetone Oxime Ether via exo-palladacycle
Direct ortho-c H Functionalization of Aromatic Alcohols Masked by Acetone Oxime Ether via exo-palladacycle Kun Guo, Xiaolan Chen, Mingyu Guan, and Yingsheng Zhao* Key Laboratory of Organic Synthesis of
More informationSupporting Information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Supporting Information Ruixuan R. Yu, Santosh K. Mahto, Kurt Justus, Mallory
More informationThiol-Ene Photoimmobilization of Chymotrypsin on Polysiloxane Gels for Enzymatic Peptide Synthesis
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Supporting information for: Thiol-Ene Photoimmobilization of Chymotrypsin on Polysiloxane Gels
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 informationAA s are the building blocks of proteins
Chamras Chemistry 106 Lecture otes Chapter 24: Amino Acids, Peptides, and Proteins General Formula: () n (') α-amino Acids: (n = 1) Example: Amino Acids and Proteins: Glycine Alanine Valine AA s are the
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 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 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 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
Supporting information Antibacterial peptide nucleic acid - antimicrobial peptide (PNA-AMP) conjugates: Antisense targeting of bacterial fatty acid biosynthesis Anna Mette Hansen, Gitte Bonke, Camilla
More informationElectronic supplementary information Poly(vinyl)chloride supported palladium nanoparticles: Catalyst for rapid hydrogenation reactions
Electronic supplementary information Poly(vinyl)chloride supported palladium nanoparticles: Catalyst for rapid hydrogenation reactions Hosahalli P. Hemantha and Vommina V. Sureshbabu* Peptide Research
More informationThe distribution of log 2 ratio (H/L) for quantified peptides. cleavage sites in each bin of log 2 ratio of quantified. peptides
Journal: Nature Methods Article Title: Corresponding Author: Protein digestion priority is independent of their abundances Mingliang Ye and Hanfa Zou Supplementary Figure 1 Supplementary Figure 2 The distribution
More informationSelective Functionalization of Antimycin A Through an N- Transacylation Reaction. Arnaud Chevalier, Yanmin Zhang, Omar M. Khdour and Sidney M.
Supporting Information Selective Functionalization of Antimycin A Through an - Transacylation Reaction for Arnaud Chevalier, Yanmin Zhang, mar M. Khdour and Sidney M. echt 1 Figure S1. Chemical structures
More informationSupporting Information
Electronic Supplementary Material (ESI) for Nanoscale. This journal is The Royal Society of Chemistry 2017 Supporting Information X-Ray Responsive Nanoparticles with Triggered Release of Nitrite, a Precursor
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 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 information