title: Synthesis of neoglycoconjugates by the desulfurative rearrangement of allylic disulfides.
abstract: Two series of neoglycosyl donors are prepared on the basis of connection of an allylic disulfide motif to the anomeric center via a simple O-glycosyl linkage or N-glycosyl amide unit. Conjugation of both sets of donors to cysteine in peptides is demonstrated through classical disulfide exchange followed by the phosphine-mediated desulfurative allylic rearrangement resulting in neoglycopeptides characterized by a simple thioether spacer. The conjugation reaction functions in the absence of protecting groups on both the neoglycosyl donor and peptide in aqueous media at room temperature.
authors: Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA. dcrich@chem.wayne.edu
authors: David
authors: D
authors: Crich
authors: Fan
authors: F
authors: Yang
mesh_terms: D000498:Allyl Compounds; D003545:Cysteine / Q000737:chemistry; D004220:Disulfides / Q000737:chemistry*; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D008968:Molecular Conformation; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry; D010455:Peptides / Q000737:chemistry
chemical_list: D000498:Allyl Compounds; D004220:Disulfides; D006001:Glycoconjugates; D009943:Organophosphorus Compounds; D010455:Peptides; C061896:triphenylphosphine; C028009:diallyl disulfide; D003545:Cysteine