Products Cited in Publications Worldwide Improved preparative enzymatic glycosylation of vancomycin aglycon and analogues

Improved preparative enzymatic glycosylation of vancomycin aglycon and analogues

Moore, Maxwell J.; Qin, Pengjin; Keith, D. Jamin; Boger, Dale L.

DOI: PMID:

Abstract

Modifications to the enzymic glycosylation of vancomycin and its residue 4 thioamide analog 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-1 g scales) and vancomycin aglycon itself (5 mg scale, 84%).

Keywords

Vancomycin ; Vancomycin analogues ; Enzymatic glycosylation

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