title: Chemoenzymatic synthesis of HIV-1 V3 glycopeptides carrying two N-glycans and effects of glycosylation on the peptide domain.
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.
authors.affiliation: Institute of Human Virology and Medical Biotechnology Center, University of Maryland Biotechnology Institute, University of Maryland, 725 W. Lombard Street, Baltimore, Maryland 21201, USA.
authors.forename: Hengguang
authors.initials: H
authors.lastname: Li
authors.forename: Bing
authors.initials: B
authors.lastname: Li
authors.forename: Haijing
authors.initials: H
authors.lastname: Song
authors.forename: Leonid
authors.initials: L
authors.lastname: Breydo
authors.forename: Ilia V
authors.initials: IV
authors.lastname: Baskakov
authors.forename: Lai-Xi
authors.initials: LX
authors.lastname: Wang
mesh_terms: D000595:Amino Acid Sequence; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015699:HIV Envelope Protein gp120 / Q000737:chemistry*; D008969:Molecular Sequence Data; D010446:Peptide Fragments / Q000737:chemistry*; D011134:Polysaccharides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006020:Glycopeptides; D015699:HIV Envelope Protein gp120; D010446:Peptide Fragments; D011134:Polysaccharides