通过串联糖基转移酶催化的反转性和新糖基化对天然产物二糖进行工程改造。
Natural product disaccharide engineering through tandem glycosyltransferase catalysis reversibility and neoglycosylation.
机构信息
Pharmaceutical Sciences Division, School of Pharmacy, Wisconsin Center for Natural Products Research, University of Wisconsin-Madison, 777 Highland Avenue, Madison, Wisconsin 53705-2222, USA.
出版信息
Org Lett. 2012 Oct 5;14(19):5086-9. doi: 10.1021/ol3023374. Epub 2012 Sep 17.
Abstract
A two-step strategy for disaccharide modulation using vancomycin as a model is reported. The strategy relies upon a glycosyltransferase-catalyzed 'reverse' reaction to enable the facile attachment of an alkoxyamine-bearing sugar to the vancomycin core. Neoglycosylation of the corresponding aglycon led to a novel set of vancomycin 1,6-disaccharide variants. While the in vitro antibacterial properties of corresponding vancomycin 1,6-disaccharide analogs were equipotent to the parent antibiotic, the chemoenzymatic method presented is expected to be broadly applicable.
摘要
本文报道了一种两步策略，使用万古霉素作为模型来调节二糖。该策略依赖于糖基转移酶催化的“反向”反应，从而能够轻松地将带有烷氧基胺的糖连接到万古霉素核心上。相应的去糖基化产物的糖基化导致了一组新型的万古霉素 1,6-二糖变体。虽然相应的万古霉素 1,6-二糖类似物的体外抗菌性能与母体抗生素相当，但所提出的化学酶法预计具有广泛的适用性。
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