Synthetic studies on glycosphingolipids from the Protostomia phyla: syntheses of arthro-series glycosphingolipids

Isao Ohtsuka; Noriyasu Hada; Mutsumi Sugita; Tadahiro Takeda

doi:10.1016/s0008-6215(02)00295-1

Synthetic studies on glycosphingolipids from the Protostomia phyla: syntheses of arthro-series glycosphingolipids

Carbohydr Res. 2002 Nov 19;337(21-23):2037-47. doi: 10.1016/s0008-6215(02)00295-1.

Authors

Isao Ohtsuka¹, Noriyasu Hada, Mutsumi Sugita, Tadahiro Takeda

Affiliation

¹ Kyoritsu College of Pharmacy, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan.

PMID: 12433469
DOI: 10.1016/s0008-6215(02)00295-1

Abstract

Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar, have quite unique structures containing GlcNAcbeta-(1 --> 3)-Man and GalNAcbeta-(1 --> 4)-GlcNAcbeta-(1 --> 3)-Man. We have synthesized two glycosphingolipids, beta-D-GlcNAcp-(1 --> 3)-beta-D-Manp-(1 --> 4)-beta-D-Glcp-(1 --> 1)-Cer and beta-D-GalNAcp-(1 --> 4)-beta-D-GlcNAcp-(1 --> 3)-beta-D-Manp-(1 --> 4)-beta-D-Glcp-(1 --> 1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the beta-mannopyranosidic linkages.

Publication types

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

MeSH terms

Animals
Ascaris suum / chemistry*
Fucose
Glycosphingolipids / chemical synthesis*
Invertebrates / chemistry
Magnetic Resonance Spectroscopy
Mannose
Monosaccharides / chemical synthesis
Oligosaccharides / chemical synthesis

Substances

Glycosphingolipids
Monosaccharides
Oligosaccharides
Fucose
Mannose