Disulfide Formation Strategies in Peptide Synthesis

作者: Tobias M. Postma , Fernando Albericio

DOI: 10.1002/EJOC.201402149

关键词:

摘要: Disulfide bonds play an important role in both proteins and peptides. They cause conformational constraints increase the stability of such molecules. In nature, disulfide are very common animal plant peptide toxins. These disulfide-rich peptides typically bind selectively with high affinities to their targets. Disulfide-rich great importance as potential therapeutics. Robust, convenient, efficient methods needed order prepare facilitate drug discovery process. This microreview explores new cysteine protecting groups that replace obsolete groups, reduce racemization, or regioselective formation, formation strategies assist synthesis complex peptides, use selenocysteine direct formation.

参考文章(85)
Glenn F King, Venoms as a platform for human drugs: translating toxins into therapeutics Expert Opinion on Biological Therapy. ,vol. 11, pp. 1469- 1484 ,(2011) , 10.1517/14712598.2011.621940
Christine Allmang, Laurence Wurth, Alain Krol, The selenium to selenoprotein pathway in eukaryotes: more molecular partners than anticipated. Biochimica et Biophysica Acta. ,vol. 1790, pp. 1415- 1423 ,(2009) , 10.1016/J.BBAGEN.2009.03.003
Zedu Huang, Darren J. Derksen, John C. Vederas, Preparation and use of cysteine orthoesters for solid-supported synthesis of peptides. Organic Letters. ,vol. 12, pp. 2282- 2285 ,(2010) , 10.1021/OL100645T
David J. Craik, Protein folding: Turbo-charged crosslinking Nature Chemistry. ,vol. 4, pp. 600- 602 ,(2012) , 10.1038/NCHEM.1417
Harold E. Swaisgood, The importance of disulfide bridging. Biotechnology Advances. ,vol. 23, pp. 71- 73 ,(2005) , 10.1016/J.BIOTECHADV.2004.09.004
Miriam Royo, Jordi Alsina, Ernest Giralt, Urszula Slomcyznska, Fernando Albericio, S-Phenylacetamidomethyl (Phacm): an orthogonal cysteine protecting group for Boc and Fmoc solid-phase peptide synthesis strategies Journal of The Chemical Society-perkin Transactions 1. pp. 1095- 1102 ,(1995) , 10.1039/P19950001095
Nico Kotzur, Benoît Briand, Michael Beyermann, Volker Hagen, Wavelength-selective photoactivatable protecting groups for thiols. Journal of the American Chemical Society. ,vol. 131, pp. 16927- 16931 ,(2009) , 10.1021/JA907287N
Bradley L. Nilsson, Matthew B. Soellner, Ronald T. Raines, Chemical synthesis of proteins. Annual Review of Biophysics and Biomolecular Structure. ,vol. 34, pp. 91- 118 ,(2005) , 10.1146/ANNUREV.BIOPHYS.34.040204.144700
Hyejung Mok, Tae Gwan Park, Self-crosslinked and reducible fusogenic peptides for intracellular delivery of siRNA Biopolymers. ,vol. 89, pp. 881- 888 ,(2008) , 10.1002/BIP.21032