Li Hengguang, Li Bing, Song Haijing, Breydo Leonid, Baskakov Ilia V, Wang Lai-Xi
Institute of Human Virology and Medical Biotechnology Center, University of Maryland Biotechnology Institute, University of Maryland, 725 W. Lombard Street, Baltimore, Maryland 21201, USA.
J Org Chem. 2005 Nov 25;70(24):9990-6. doi: 10.1021/jo051729z.
[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.
[结构：见正文] 实现了携带两个N-连接核心三糖和五糖的HIV-1 V3结构域糖肽的高效化学酶促合成。该合成包括两个关键步骤：固相合成含有两个N-乙酰葡糖胺残基的环状47肽V3结构域肽，以及一种新型内切糖苷酶催化的转糖基化反应，该反应同时从寡糖恶唑啉供体底物向肽前体添加两个N-聚糖部分。合成糖肽的可得性使得能够探究糖基化对HIV-1 V3结构域的影响。结果表明，糖基化影响V3结构域的整体构象，并为V3结构域提供抗蛋白酶消化的保护作用。
