Direct on-resin synthesis of peptide-alphathiophenylesters for use in native chemical ligation

Organic Letters
Duhee BangStephen B H Kent

Abstract

[reaction: see text] A peptide-(alpha)thiophenylester is a key reactant in native chemical ligation. Preformation of the peptide-(alpha)thiophenylester could be useful for enhancing the ligation reaction. We report the direct on-resin preparation of preformed peptide-(alpha)thiophenylesters using a simple and efficient method. The peptide-(alpha)thiophenylester reacted extremely rapidly with a Cys-peptide when compared to the peptide-(alpha)thioalkylester.

References

May 3, 1972·Journal of the American Chemical Society·B F Gisin, R B Merrifield
Nov 4, 1994·Science·P E DawsonS B Kent
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

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Citations

Mar 16, 2007·Proceedings of the National Academy of Sciences of the United States of America·Thomas DurekStephen B H Kent
Sep 28, 2016·Chemical Reviews·Renata Marcia de FigueiredoJean-Marc Campagne
Sep 23, 2016·Angewandte Chemie·Richard RazJohn Offer
Oct 15, 2011·Angewandte Chemie·Thomas Durek, Paul F Alewood
Aug 29, 2012·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Akira OtakaAkira Shigenaga
Dec 17, 2008·Angewandte Chemie·Christian P R Hackenberger, Dirk Schwarzer
Feb 17, 2010·Chembiochem : a European Journal of Chemical Biology·Ji-Shen ZhengLei Liu
Apr 20, 2010·Chembiochem : a European Journal of Chemical Biology·Ge-Min FangLei Liu
Mar 3, 2011·Chemistry, an Asian Journal·Chen WangYao Fu
Feb 23, 2007·Organic & Biomolecular Chemistry·Tyrone J HogenauerKatja Michael
Feb 13, 2020·Organic & Biomolecular Chemistry·Victor V YimMargaret A Brimble
Aug 1, 2015·Chembiochem : a European Journal of Chemical Biology·Andrew PardoKatja Michael
Jul 9, 2011·Chembiochem : a European Journal of Chemical Biology·Kohei SatoAkira Otaka
Sep 13, 2011·Chembiochem : a European Journal of Chemical Biology·Santosh K MahtoJennifer J Ottesen
May 26, 2017·Nature Communications·Helen M BurkeEoin M Scanlan
Nov 13, 2010·Chemical Communications : Chem Comm·Lingliang LongLin Yuan
Jul 18, 2012·The Journal of Organic Chemistry·Hironobu HojoYoshiaki Nakahara
May 16, 2015·Journal of the American Chemical Society·Juan B Blanco-CanosaPhilip E Dawson

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