A new approach for the synthesis of hyperbranched N-glycan core structures from locust bean gum

H V Ravi Kumar; Kentaro Naruchi; Risho Miyoshi; Hiroshi Hinou; Shin-Ichiro Nishimura

doi:10.1021/ol403140h

A new approach for the synthesis of hyperbranched N-glycan core structures from locust bean gum

Org Lett. 2013 Dec 20;15(24):6278-81. doi: 10.1021/ol403140h. Epub 2013 Nov 21.

Authors

H V Ravi Kumar¹, Kentaro Naruchi, Risho Miyoshi, Hiroshi Hinou, Shin-Ichiro Nishimura

Affiliation

¹ Division of Drug Discovery Research, Faculty of Advanced life Science and Graduate School of Life Science, Hokkaido University , N21, W11, Kita-ku, Sapporo 001-0021, Japan, and Medicinal Chemistry Pharmaceuticals, Co. Ltd., N21, W12, Kita-ku, Sapporo 001-0021, Japan.

PMID: 24261553
DOI: 10.1021/ol403140h

Abstract

A novel protocol for the synthesis of general N-glycan core structures was established by means of Manβ(1→4)Man peracetate derived from a naturally abundant locust bean gum as a key starting material. Phenyl (2-O-benzyl-4,6-O-benzylidine-β-D-mannopyranosyl)-(1→4)-3,6-di-O-benzyl-2-azido-2-deoxy-1-thio-β-D-glucopyranoside facilitated the synthesis of key intermediates leading to hyperbranched N-glycan core structures.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrate Conformation
Galactans / chemistry*
Mannans / chemistry*
Molecular Sequence Data
Plant Gums / chemistry*
Polysaccharides / chemical synthesis*
Polysaccharides / chemistry

Substances

Galactans
Mannans
Plant Gums
Polysaccharides
locust bean gum