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

被引:70
作者
Li, HG
Li, B
Song, HJ
Breydo, L
Baskakov, IV
Wang, LX
机构
[1] Univ Maryland, Inst Human Virol, Baltimore, MD 21201 USA
[2] Univ Maryland, Ctr Med Biotechnol, Baltimore, MD 21201 USA
[3] Univ Maryland, Inst Biotechnol, Baltimore, MD 21201 USA
关键词
D O I
10.1021/jo051729z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:9990 / 9996
页数:7
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