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One‐Pot Protection Strategy of Glucosamine to Assemble Building Blocks of Chitosan and Lipid A
Author(s) -
Chen JyunSiao,
Pantawane Amit Ravindra,
Huang PoHsun,
Liu JenWei,
Sankar Arumugam,
Lin YiJyun,
Liu YuHao,
Wu HsinRu,
Luo ShunYuan
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000923
Subject(s) - chemistry , glycosyl , glucosamine , glycosylation , glycopeptide , disaccharide , alcohol , chitosan , combinatorial chemistry , glycosyl donor , stereochemistry , organic chemistry , biochemistry , antibiotics
This investigation describes a one‐pot reaction to prepare a series of building blocks for glycosylation reactions, such as 3‐alcohol glucosamines, fully protected glucosamines, O‐ 4 and O‐ 6 alcohol glucosamines. These reactions readily produce not only glycosyl donors and acceptors, but also different glycosyl units that can be changed based on the needs of the experiment. The synthesis of some molecules containing glucosamines, including saccharide chains of glycopeptide (GP) and precursors of lipid A disaccharide backbone, are also described. GP has good selectivity for tumor angiogenesis and this phenomenon makes the GP a potential target drug. Lipid A has recently been adopted as an adjuvant for human vaccines.