Trends in Glycoscience and Glycotechnology
Online ISSN : 1883-2113
Print ISSN : 0915-7352
ISSN-L : 0915-7352
GLYCODEBUT
Semisynthesis of Complex-type Triantennary Oligosaccharides from a Biantennary Oligosaccharide Isolated from Hen Egg Yolk
Yuta Maki
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2018 Volume 30 Issue 171 Pages E15-E20

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Abstract

Oligosaccharides of glycoproteins have important functions in many biological processes. Complex-type oligosaccharides are major structures of asparagine-linked oligosaccharides and have unique antennary structures, such as bi-, tri-, and tetra-antennary forms. Here, we describe a novel method for semisynthesis of two types of naturally occurring complex-type triantennary oligosaccharides, 1 and 2, in 9 and 10 conversion steps, respectively. The semisynthesis employed a biantennary oligosaccharide isolated from a natural source as a starting material. A benzylidenation reaction enabled selective protection of 8 hydroxy groups, among the 24 hydroxy groups of the biantennary oligosaccharide. Furthermore, selective debenzylidenation of mannoside residues successfully produced two types of suitably protected oligosaccharyl acceptors. Glycosylation with a disaccharide donor and subsequent deprotection steps yielded two types of intact complex-type triantennary oligosaccharides.

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© 2018 FCCA (Forum: Carbohydrates Coming of Age)
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