Microwave-mediated reduction of disulfide bridges with supported (tris(2-carboxyethyl)phosphine) as resin-bound reducing agent

ACS Combinatorial Science

Volumn 15, Issue 4, 2013, Pages 169-173

  Miralles, Guillaume ^a   Verdié, Pascal ^a   Puget, Karine ^b   Maurras, Amélie ^b   Martinez, Jean ^a   Subra, Gilles ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b Les Coteaux Saint Roch   (France)

Author keywords

cysteine; disulfide bond; reduction; supported reagent; TCEP; thiol

Indexed keywords

DISULFIDE; PEPTIDE; PHOSPHINE DERIVATIVE; REDUCING AGENT; TRIS(2 CARBOXYETHYL)PHOSPHINE; TRIS(2-CARBOXYETHYL)PHOSPHINE;

AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; MICROWAVE RADIATION; MOLECULAR GENETICS; OXIDATION REDUCTION REACTION; SYNTHESIS;

AMINO ACID SEQUENCE; DISULFIDES; MICROWAVES; MOLECULAR SEQUENCE DATA; OXIDATION-REDUCTION; PEPTIDES; PHOSPHINES; REDUCING AGENTS;

EID: 84875980335     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co300104k     Document Type: Article

References (23)

1. Han, J. C.; Han, G. Y. A procedure for quantitative determination of tris(2-carboxyethyl)phosphine, an odorless reducing agent more stable and effective than dithiothreitol Anal. Biochem. 1994, 220, 5-10
2. Nobs, L.; Buchegger, F.; Gurny, R.; Allémann, E. Surface modification of poly(lactic acid) nanoparticles by covalent attachment of thiol groups by means of three methods Int. J. Pharm. 2003, 250, 327-337
3. Kirley, T. L. Reduction and fluorescent labeling of cyst(e)ine-containing proteins for subsequent structural analyses Anal. Biochem. 1989, 180, 231-236
4. Oda, Y.; Nagasu, T.; Chait, B. T. Enrichment analysis of phosphorylated proteins as a tool for probing the phosphoproteome Nat. Biotechnol. 2001, 19, 379-382
5. Visser, C. C.; Heleen Voorwinden, L.; Harders, L. R.; Eloualid, M.; Van Bloois, L.; Crommelin, D. J. A.; Danhof, M.; De Boer, A. G. Coupling of metal containing homing devices to liposomes via a maleimide linker: Use of TCEP to stabilize thiol-groups without scavenging metals J. Drug Targeting 2004, 12, 569-573
6. Schumacher, F. F.; Nobles, M.; Ryan, C. P.; Smith, M. E. B.; Tinker, A.; Caddick, S.; Baker, J. R. In situ maleimide bridging of disulfides and a new approach to protein PEGylation Bioconjugate Chem. 2011, 22, 132-136
7. Singha, N. K.; Gibson, M. I.; Koiry, B. P.; Danial, M.; Klok, H.-A. Side-chain peptide-synthetic polymer conjugates via tandem "ester-amide/ thiol-ene" post-polymerization modification of poly(pentafluorophenyl methacrylate) obtained using ATRP Biomacromolecules 2011, 12, 2908-2913
8. Schelté; Boeckler, C.; Frisch, B.; Schuber, F. Differential reactivity of maleimide and bromoacetyl functions with thiols: Application to the preparation of liposomal diepitope constructs Bioconjugate Chem. 1999, 11, 118-123
9. Chen, X.; Qoutah, W. W.; Free, P.; Hobley, J.; Fernig, D. G.; Paramelle, D. Features of thiolated ligands promoting resistance to ligand exchange in self-assembled monolayers on gold nanoparticles Aust. J. Chem. 2012, 65, 266-274
10. MacBeath, G.; Koehler, A. N.; Schreiber, S. L. Printing small molecules as microarrays and detecting protein-ligand interactions en masse J. Am. Chem. Soc. 1999, 121, 7967-7968
11. Eom, K. D.; Miao, Z.; Yang, J.-L.; Tam, J. P. Tandem ligation of multipartite peptides with cell-permeable activity J. Am. Chem. Soc. 2002, 125, 73-82
12. Nefzi, A.; Sun, X.; Mutter, M. Chemoselective ligation of multifunctional peptides to topological templates via thioether formation for TASP synthesis Tetrahedron Lett. 1995, 36, 229-230
13. Foillard, S.; Sancey, L.; Coll, J.-L.; Boturyn, D.; Dumy, P. Targeted delivery of activatable fluorescent pro-apoptotic peptide into live cells Org. Biomol. Chem. 2009, 7, 221
14. Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. Synthesis of proteins by native chemical ligation Science 1994, 266, 776-779
15. Dheur, J.; Ollivier, N.; Vallin, A.; Melnyk, O. Synthesis of peptide alkylthioesters using the intramolecular N, S -acyl shift properties of bis(2-sulfanylethyl)amido peptides J. Org. Chem. 2011, 76, 3194-3202
16. Ollivier, N.; Dheur, J.; Mhidia, R.; Blanpain, A.; Melnyk, O. Bis(2-sulfanylethyl)amino native peptide ligation Org. Lett. 2010, 12, 5238-5241
17. Han, J.; Clark, C.; Han, G.; Chuand, T.-C.; Han, P. Preparation of 2-nitro-5-thiobenzoic acid using immobilized tris(2-carboxyethyl)phosphine Anal. Biochem. 1999, 268, 404-407
18. Rana, S.; White, P.; Bradley, M. Influence of resin cross-linking on solid-phase chemistry J. Comb. Chem. 2000, 3, 9-15
19. Amblard, M.; Fehrentz, J.-A.; Martinez, J.; Subra, G. Methods and protocols of modern solid-phase peptide synthesis Mol. Biotechnol. 2006, 33, 239-254
20. García-Ramos, Y.; Paradís-Bas, M.; Tulla-Puche, J.; Albericio, F. ChemMatrix for complex peptides and combinatorial chemistry J. Pept. Sci. 2010, 16, 675-678
21. Machado, A.; Fázio, M. A.; Miranda, A.; Daffre, S.; Machini, M. T. Synthesis and properties of cyclic gomesin and analogues J. Pept. Sci. 2012, 18, 588-598
22. Ozaki, A.; Ariki, S.; Kawabata, S. An antimicrobial peptide tachyplesin acts as a secondary secretagogue and amplifies lipopolysaccharide-induced hemocyte exocytosis FEBS J. 2005, 272, 3863-3871
23. Morisset, D.; Frère, J. Heterologous expression of bacteriocins using the mesentericin Y105 dedicated transport system by Leuconostoc mesenteroides Biochimie 2002, 84, 569-576