BioChem - DOS

Chemoenzymatic Synthesis of a Library of Human Milk Oligosaccharides

Journal of organic chemistry

Xiao, Zhongying; Guo, Yuxi; Liu, Yunpeng; Li, Lei; Zhang, Qing; Wen, Liuqing; Wang, Xuan; Kondengaden, Shukkoor Muhammed; Wu, Zhigang; Zhou, Jun; Cao, Xuefeng; Li, Xu; Ma, Cheng; Wang, Peng George

<P>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.</P><P><B>Graphic Abstract</B><BR><IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/joceah/2016/joceah.2016.81.issue-14/acs.joc.6b00478/production/images/medium/jo-2016-00478r_0011.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/jo6b00478'>ACS Electronic Supporting Info</A></P>

2016

American Chemical Society

0022-3263

1520-6904

81

14

pp.5851-5865

10.1021/acs.joc.6b00478

http://click.ndsl.kr/servlet/OpenAPIDetailView?keyValue=05787966&target=NART&cn=NART75960755

https://europepmc.org/articles/pmc5953189?pdf=render