A convergent synthesis of trisaccharides with alpha-Neu5Ac-(2 -> 3)-beta-D-Gal-(1 -> 4)-beta-D-GlcNAc and alpha-Neu5Ac-(2 -> 3)-beta-D-Gal-(1 -> 3)-alpha-D-GalNAc sequences

Authors
Xia, J Alderfer, JL Piskorz, CF Locke, RD Matta, KL
Citation
J. Xia et al., A convergent synthesis of trisaccharides with alpha-Neu5Ac-(2 -> 3)-beta-D-Gal-(1 -> 4)-beta-D-GlcNAc and alpha-Neu5Ac-(2 -> 3)-beta-D-Gal-(1 -> 3)-alpha-D-GalNAc sequences, CARBOHY RES, 328(2), 2000, pp. 147-163
Citations number
42
Categorie Soggetti
Agricultural Chemistry","Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
CARBOHYDRATE RESEARCH
ISSN journal
00086215 → ACNP
Volume
328
Issue
2
Year of publication
2000
Pages
147 - 163
Database
ISI
SICI code
0008-6215(20000908)328:2<147:ACSOTW>2.0.ZU;2-V
Abstract
The syntheses of three trisaccharides: alpha-Neu5Ac-(2 --> 3)-beta-D-Gal-(1 --> 4)-beta-D-GlcNAc --> OMe, alpha-Neu5Ac-(2 --> 3)-beta-D-Gal6SO(3)Na-(1 --> 4)-beta-D-GlNAc --> OMe, and alpha-Neu5Ac-(2 --> 3)-beta-D-Gal-(1 --> 3)-alpha-D-GalNAc --> OBn were accomplished by using either methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-beta-D-glycero-D-gala cto-2-nonulopyranoside)onate or methyl (phenyl N-acetyl-5-acetamido-4,7,8,9 -tetra-O-acetyl-3,5-dideoxy-2-thio-beta-D-glycero-D-galacto-2-nonulopyranos ide)onate as th sialyl donor. The N,N-diacetylamino sialyl donor appears to be more reactive than its parent acetamido sugar when allowed to react an disaccharide acceptor under the same glycosylation conditions. The trisacch arides, as well as the intermediate products, were fully characterized by 2 D DQF H-1-H-1 COSY and 2D ROESY spectroscopy. (C) 2000 Elsevier Science Ltd . All rights reserved.