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.

SUBMITTER: Crich D 

PROVIDER: S-EPMC2742710 | biostudies-literature | 2008 Sep

REPOSITORIES: biostudies-literature