Synthesis and NMR assignments of galactosylgloboside and its beta-D-GalNAc-(1 -> 4)-alpha-D-Gal-linked positional isomer in a conjugatable form

Authors
Zou, W Brisson, JR Larocque, S Gardner, RL Jennings, HJ
Citation
W. Zou et al., Synthesis and NMR assignments of galactosylgloboside and its beta-D-GalNAc-(1 -> 4)-alpha-D-Gal-linked positional isomer in a conjugatable form, CARBOHY RES, 315(3-4), 1999, pp. 251-261
Citations number
34
Categorie Soggetti
Agricultural Chemistry","Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
CARBOHYDRATE RESEARCH
ISSN journal
00086215 → ACNP
Volume
315
Issue
3-4
Year of publication
1999
Pages
251 - 261
Database
ISI
SICI code
0008-6215(19990228)315:3-4<251:SANAOG>2.0.ZU;2-A
Abstract
Two pentasaccharides suitable for conjugation, namely 3-aminopropyl glactos ylgloboside and its beta-D-GalNAc-(1 -->4)-alpha-D-Gal-linked positional is omer, were synthesized from 3(III),4(III)-di-O-unprotected globotrioside an d the trichloroacetimidate of beta-D-Gal-(1 --> 3)-beta-D-GalNPhth derivati ve. Glycosylation at both positions led to the formation of beta-D-GalNPhth -(1-->4)-alpha-D-Gal and beta-D-GalNPhth-(1-->3)-alpha-D-Gal-linked product s in a ratio of 1:1 without selectivity. Complete NMR spectral assignments are also described. (C) 1999 Elsevier Science Ltd. All rights reserved.