Sugar-assisted glycopeptide ligation

Journal of the American Chemical Society
Ashraf BrikChi-Huey Wong

Abstract

The chemical synthesis of glycopeptides and glycoproteins from readily available materials presents an attractive route to homogeneous products for structural and functional studies. Chemical synthesis of glycopeptides and glycoproteins based on native chemical ligation represents one of the useful methods for the synthesis of natural glycopeptide structures. Here we describe a method that allows for the synthesis of glycopeptides from cysteine-free peptides. This method utilizes a peptide thioester and a glycopeptide in which the sugar moiety is modified with a thiol handle at the C-2 position. Upon completion of the ligation reaction, the thiol handle can be reduced with H2/metal to the acetamide moiety, furnishing the unmodified glycopeptides. Together, this sequence of reactions displays an attractive potential in glycopeptides and glycoproteins synthesis.

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Citations

May 26, 2007·Journal of the American Chemical Society·Yu-Ying YangChi-Huey Wong
Aug 14, 2008·Journal of the American Chemical Society·Clay S BennettChi-Huey Wong
Jun 14, 2013·The Journal of Organic Chemistry·Vadim PopovAlan R Katritzky
Mar 1, 2012·Organic Letters·Peter SimanAshraf Brik
Mar 1, 2008·Chemical Communications : Chem Comm·Marina-Yamit LutskyAshraf Brik
Jul 9, 2009·Chemical Communications : Chem Comm·Gemma L Thomas, Richard J Payne
Nov 12, 2009·Chemical Communications : Chem Comm·James GarnerRichard J Payne
Apr 20, 2011·Chemical Communications : Chem Comm·Chung-Yi Wu, Chi-Huey Wong
Jun 16, 2012·The Journal of Biological Chemistry·James P Tam, Clarence T T Wong
Sep 29, 2012·Beilstein Journal of Organic Chemistry·Workalemahu M BerhanuAlan R Katritzky
Dec 9, 2008·Current Opinion in Chemical Biology·Anouk Dirksen, Philip E Dawson
Dec 21, 2012·Chemical Biology & Drug Design·Justin M Chalker
Sep 24, 2010·Journal of Peptide Science : an Official Publication of the European Peptide Society·K S Ajish Kumar, Ashraf Brik
Dec 5, 2012·Chemical Biology & Drug Design·Bahaa El-Dien M El-GendyAlan R Katritzky
Mar 11, 2011·Journal of Peptide Science : an Official Publication of the European Peptide Society·Liat SpasserAshraf Brik
Sep 15, 2012·Chemical Biology & Drug Design·Siva S PandaAlan R Katritzky
Nov 29, 2013·Journal of Peptide Science : an Official Publication of the European Peptide Society·Lara R MalinsRichard J Payne
Oct 2, 2015·Organic Letters·Marianne FouchéHans-Jörg Roth
Mar 17, 2016·Journal of the American Chemical Society·Yue GuiSuwei Dong
Aug 9, 2015·Proceedings of the National Academy of Sciences of the United States of America·Chin-Wei LinChi-Huey Wong
May 15, 2016·Molecular Aspects of Medicine·Larissa Krasnova, Chi-Huey Wong
May 6, 2016·Annual Review of Biochemistry·Larissa Krasnova, Chi-Huey Wong
Oct 19, 2006·Current Opinion in Chemical Biology·Ashraf BrikChi-Huey Wong
Oct 15, 2013·Journal of Peptide Science : an Official Publication of the European Peptide Society·Yi-Tong LiLei Liu
Aug 29, 2012·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Akira OtakaAkira Shigenaga
May 18, 2007·Chemistry : a European Journal·Ashraf Brik, Chi-Huey Wong
Feb 19, 2008·Chemistry : a European Journal·Simon FichtChi-Huey Wong
Apr 30, 2008·Angewandte Chemie·Richard J PayneChi-Huey Wong
Jul 16, 2008·Angewandte Chemie·Christian HaaseOliver Seitz
Dec 17, 2008·Angewandte Chemie·Christian P R Hackenberger, Dirk Schwarzer
Sep 26, 2009·Angewandte Chemie·K S Ajish KumarAshraf Brik
Apr 20, 2010·Chembiochem : a European Journal of Chemical Biology·Ge-Min FangLei Liu
May 4, 2010·Chembiochem : a European Journal of Chemical Biology·Ziv HarpazAshraf Brik
Mar 3, 2011·Chemistry, an Asian Journal·Chen WangYao Fu
Dec 22, 2009·Chemical Communications : Chem Comm·Richard J Payne, Chi-Huey Wong

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