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Enzymatic Synthesis of Human Milk Fucosides α1,2‐Fucosyl para ‐Lacto‐ N ‐Hexaose and its Isomeric Derivatives
Author(s) -
Fang JiaLin,
Tsai TengWei,
Liang ChinYu,
Li JyunYi,
Yu ChingChing
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800518
Subject(s) - chemistry , fucosylation , glycosylation , enzyme , glycosyltransferase , glycan , stereochemistry , biochemistry , oligosaccharide , fucosyltransferase , combinatorial chemistry , glycoprotein
Enzymatic synthesis of para ‐lacto‐ N ‐hexaose and its isomeric structures as well as those α1,2‐fucosylated variants naturally occurring in human milk oligosaccharide (HMOs) was achieved using a sequential one‐pot enzymatic system. Three glycosylation routes comprising bacterial glycosyltransferases and corresponding sugar‐nucleotide‐generating enzymes were developed to facilitate efficient production of extended type‐1 and type‐2 N ‐acetyllactosamine (LacNAc) backbones and hybrid chains. Further fucosylation efficiency of two α1,2‐fucosyltransferases on both type‐1 and type‐2 chains of the hexasaccharide was investigated to achieve practical synthesis of the fucosylated glycans. The availability of structurally defined HMOs offers a practical approach for investigating future biological applications.