Chemoenzymatic Synthesis of a Library of Human Milk Oligosaccharides

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• 作者：Zhongying Xiao ; Yuxi Guo ; Yunpeng Liu ; Lei Li ; Qing Zhang ; Liuqing Wen ; Xuan Wang ; Shukkoor Muhammed Kondengaden ; Zhigang Wu ; Jun Zhou ; Xuefeng Cao ; Xu Li ; Cheng Ma ; Peng George Wang
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：July 15, 2016
• 年：2016
• 卷：81
• 期：14
• 页码：5851-5865
• 全文大小：838K
• 年卷期：0
• ISSN：1520-6904

文摘

Human milk oligosaccharides (HMOs) are a family of diverse unconjugated glycans that exist in human milk as one of the major components. Characterization, quantification, and biofunctional studies of HMOs remain a great challenge due to their diversity and complexity. The accessibility of a homogeneous HMO library is essential to solve these issues which have beset academia for several decades. In this study, an efficient chemoenzymatic strategy, namely core synthesis/enzymatic extension (CSEE), for rapid production of diverse HMOs was reported. On the basis of 3 versatile building blocks, 3 core structures were chemically synthesized via consistent use of oligosaccharyl thioether and oligosaccharyl bromide as glycosylation donors in a convergent fragment coupling strategy. Each of these core structures was then extended to up to 11 HMOs by 4 robust glycosyltransferases. A library of 31 HMOs were chemoenzymatically synthesized and characterized by MS and NMR. CSEE indeed provides a practical approach to harvest structurally defined HMOs for various applications.