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Chem Asian J. 2018 Jun 18;13(12):1544-1551. doi: 10.1002/asia.201800367. Epub 2018 May 25.

Convergent Synthesis of a Bisecting N-Acetylglucosamine (GlcNAc)-Containing N-Glycan.

Author information

1
Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka, 560-0043, Japan.
2
Core for Medicine and Science Collaborative Research and Education, Project Research Center for Fundamental Sciences, Graduate School of Science, Osaka University, Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan.
3
Biofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan.
4
Department of Chemical Science, University of Naples Federico II, Via Cinthia 4, 80126, Naples, Italy.

Abstract

The chemical synthesis of a bisecting N-acetylglucosamine (GlcNAc)-containing N-glycan was achieved by a convergent synthetic route through [4+2] and [6+2] glycosylations. This synthetic route reduced the number of reaction steps, although the key glycosylations were challenging in terms of yields and selectivities owing to steric hindrance at the glycosylation site and a lack of neighboring group participation. The yields of these glycosylations were enhanced by stabilizing the oxocarbenium ion intermediate through ether coordination. Glycosyl donor protecting groups were explored in an effort to realize perfect α selectivity by manipulating remote participation. The simultaneous glycosylations of a tetrasaccharide with two disaccharides was investigated to efficiently construct a bisecting GlcNAc-containing N-glycan.

KEYWORDS:

convergent synthesis; glycosylation; oligosaccharides; protecting groups; synthesis design

PMID:
29665315
DOI:
10.1002/asia.201800367

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