Chemoenzymatic synthesis of HIV-1 V3 glycopeptides carrying two N-glycans and effects of glycosylation on the peptide domain

The Journal of Organic Chemistry
Hengguang LiLai-Xi Wang

Abstract

[structure: see text] A highly efficient chemoenzymatic synthesis of HIV-1 V3 domain glycopeptides carrying two N-linked core tri- and pentasaccharides was achieved. The synthesis consisted of two key steps: a solid-phase synthesis of the cyclic, 47-mer V3 domain peptide containing two GlcNAc residues and a novel endoglycosidase-catalyzed transglycosylation that simultaneously added two N-glycan moieties to the peptide precursor from the oligosaccharide oxazoline donor substrates. The availability of the synthetic glycopeptides allowed the probing of the effects of glycosylation on the HIV-1 V3 domain. It was demonstrated that glycosylation influenced the global conformations of the V3 domain and provided protection of the V3 domain against protease digestion.

Citations

Mar 13, 2013·Bioorganic & Medicinal Chemistry·Joseph V LominoLai-Xi Wang
Dec 7, 2011·ACS Chemical Biology·Lai-Xi Wang, Joseph V Lomino
Aug 14, 2008·Journal of the American Chemical Society·Clay S BennettChi-Huey Wong
Sep 23, 2008·Journal of the American Chemical Society·Hirofumi OchiaiLai-Xi Wang
Nov 18, 2009·Journal of the American Chemical Society·Wei HuangLai-Xi Wang
Sep 28, 2012·Beilstein Journal of Organic Chemistry·Ulrika Westerlind
Jul 9, 2013·Nature Chemical Biology·Mohammed N AminLai-Xi Wang
Apr 9, 2016·Carbohydrate Research·Pragya Priyanka, Antony J Fairbanks
Jun 27, 2008·Vaccine·A H LucasC E Taylor
Jun 27, 2012·BMB Reports·Serenus Hua, Hyun Joo An
Jan 21, 2014·Chemistry & Biology·Lai-Xi Wang, Mohammed N Amin
Sep 12, 2008·Bioorganic & Medicinal Chemistry·Cishan LiLai-Xi Wang
Jun 27, 2006·Chembiochem : a European Journal of Chemical Biology·Thomas W D F RisingAntony J Fairbanks
Dec 10, 2015·Organic & Biomolecular Chemistry·Jian-Song SunJin-Xi Liao
Jun 10, 2008·Chemistry : a European Journal·Thomas W D F RisingAntony J Fairbanks
Nov 16, 2007·Organic & Biomolecular Chemistry·Vipin Kumar, Namakkal G Ramesh
Nov 14, 2014·Nature Chemical Biology·Satoru HoriyaIsaac J Krauss
Apr 1, 2015·Expert Review of Vaccines·Alberto Fernández-TejadaSamuel Danishefsky
Oct 17, 2019·Glycobiology·Jonathan SjögrenAndreas Nägeli
Aug 5, 2008·Chembiochem : a European Journal of Chemical Biology·Christoph D HeideckeAntony J Fairbanks
Feb 6, 2007·Biopolymers·Hironobu Hojo, Yoshiaki Nakahara
Jan 1, 2011·Trends in Glycoscience and Glycotechnology : TIGG·Lai-Xi Wang
Mar 17, 2017·Science Translational Medicine·S Munir AlamBarton F Haynes
Jan 26, 2013·Chemical Society Reviews·Pavla BojarováVladimír Křen
Dec 20, 2008·Chemical Reviews·David P GamblinBenjamin G Davis
Oct 15, 2009·Chemical Reviews·Shiro Kobayashi, Akira Makino
May 3, 2021·The FEBS Journal·Marko AnderluhSandra J van Vliet

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