Synthesis of cysteine-rich peptides by native chemical ligation without use of exogenous thiols

Organic Letters
Shugo TsudaYuji Nishiuchi

Abstract

Native chemical ligation (NCL) performed without resorting to the use of thiol additives was demonstrated to be an efficient and effective procedure for synthesizing Cys-rich peptides. This method using tris(2-carboxyethyl)phosphine (TCEP) as a reducing agent facilitates the ligation reaction even at the Thr-Cys or Ile-Cys site and enables one-pot synthesis of Cys-rich peptides throughout NCL and oxidative folding.

References

Feb 1, 1988·BioEssays : News and Reviews in Molecular, Cellular and Developmental Biology·T E Creighton
Nov 4, 1994·Science·P E DawsonS B Kent
Dec 19, 1995·Proceedings of the National Academy of Sciences of the United States of America·J P TamJ Shao
Apr 10, 1999·Nature Neuroscience·R S ChuangK J Swartz
Sep 1, 1999·Proceedings of the National Academy of Sciences of the United States of America·T M HackengP E Dawson
Aug 31, 2000·Annual Review of Biochemistry·P E Dawson, S B Kent
Dec 12, 2002·Biochemistry·Richard E MiddletonMcHardy M Smith
Dec 22, 2004·Biotechnology Advances·Harold E Swaisgood
Apr 20, 2006·Amino Acids·M Werle, A Bernkop-Schnürch
May 18, 2006·Journal of the American Chemical Society·Erik C B Johnson, Stephen B H Kent
Sep 6, 2006·Toxicon : Official Journal of the International Society on Toxinology·Raymond S Norton, Baldomero M Olivera
Mar 16, 2007·Proceedings of the National Academy of Sciences of the United States of America·Thomas DurekStephen B H Kent
Jan 27, 2009·Chemical Society Reviews·Stephen B H Kent
Mar 25, 2009·Toxicon : Official Journal of the International Society on Toxinology·Jonas E JensenLachlan D Rash
Aug 1, 2009·Natural Product Reports·Reena Halai, David J Craik
Aug 3, 2010·Chembiochem : a European Journal of Chemical Biology·Rodrigo A V MoralesThomas Durek
May 11, 2011·Chembiochem : a European Journal of Chemical Biology·Heike RohdeOliver Seitz
Jul 26, 2012·Current Topics in Medicinal Chemistry·Masa CemazarDavid J Craik
Oct 20, 2012·The Journal of Organic Chemistry·Helmus van de LangemheenRob M J Liskamp
Dec 11, 2013·Angewandte Chemie·Christina I SchroederThomas Durek
Mar 20, 2014·Chemistry : a European Journal·Paul W R HarrisMargaret A Brimble
May 31, 2014·Journal of the American Chemical Society·Robert E ThompsonRichard J Payne
Jul 6, 2014·Angewandte Chemie·Bobo DangStephen B H Kent

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Citations

Mar 17, 2016·Journal of the American Chemical Society·Yue GuiSuwei Dong
Aug 3, 2016·Journal of Peptide Science : an Official Publication of the European Peptide Society·Emma J Ste MarieRobert J Hondal
Sep 28, 2016·Chemical Reviews·Renata Marcia de FigueiredoJean-Marc Campagne
Apr 20, 2019·Chembiochem : a European Journal of Chemical Biology·Shugo TsudaTaku Yoshiya

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