Natural Product Disaccharide Engineering through Tandem Glycosyltransferase Catalysis Reversibility and Neoglycosylation

详细信息    查看全文

• 作者：Pauline Peltier-Pain ; Karen Marchillo ; Maoquan Zhou ; David R. Andes ; Jon S. Thorson
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：October 5, 2012
• 年：2012
• 卷：14
• 期：19
• 页码：5086-5089
• 全文大小：241K
• 年卷期：v.14,no.19(October 5, 2012)
• ISSN：1523-7052

文摘

A two-step strategy for disaccharide modulation using vancomycin as a model is reported. The strategy relies upon a glycosyltransferase-catalyzed 鈥榬everse鈥?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.