Improved preparative enzymatic glycosylation of vancomycin aglycon and analogues.

ABSTRACT: Modifications to the enzymatic glycosylation of vancomycin and its residue 4 thioamide analogue are detailed that significantly reduce the enzyme loading and amount of glycosyl donor needed for each glycosylation reaction, provide a streamlined synthesis and replacement for the synthetic UDP-vancosamine glycosyl donor to improve both access and storage stability, and permit a single-pot, two-step conversion of the aglycons to the fully glycosylated synthetic glycopeptides now conducted at higher concentrations. The improvements are exemplified with the two-step, one-pot glycosylation of [Ψ[C(=S)NH]Tpg⁴]vancomycin aglycon (92%) conducted on a 400 mg scale (2 mg to 1 g scales) and vancomycin aglycon itself (5 mg scale, 84%).

SUBMITTER: Moore MJ 

PROVIDER: S-EPMC9913888 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature