改进的万古霉素苷元及类似物的制备性酶促糖基化反应
Improved preparative enzymatic glycosylation of vancomycin aglycon and analogues.
作者信息
Moore Maxwell J, Qin Pengjin, Keith D Jamin, Boger Dale L
机构信息
Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037, USA.
出版信息
Tetrahedron. 2023 Jan 26;131. doi: 10.1016/j.tet.2022.133211. Epub 2022 Dec 12.
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]Tpg]vancomycin aglycon (92%) conducted on a 400 mg scale (2 mg to 1 g scales) and vancomycin aglycon itself (5 mg scale, 84%).
摘要
详细介绍了对万古霉素及其4-硫代酰胺类似物的酶促糖基化修饰，这些修饰显著降低了每个糖基化反应所需的酶负载量和糖基供体的量，提供了一种简化的合成方法，并替代了合成的UDP-万古糖胺糖基供体，以改善获取和储存稳定性，并且允许在更高浓度下将苷元进行单锅两步转化为完全糖基化的合成糖肽。以[Ψ[C(=S)NH]Tpg]万古霉素苷元（92%）在400 mg规模（2 mg至1 g规模）上的两步一锅糖基化以及万古霉素苷元本身（5 mg规模，84%）为例说明了这些改进。
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3
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