Synthesis of N-4-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine analogues. L-2-chloro-, L-2-bromo-, and D,L-2-methylsuccinamic acid analogues

Authors
Xia, YQ Risley, JM
Citation
Yq. Xia et Jm. Risley, Synthesis of N-4-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine analogues. L-2-chloro-, L-2-bromo-, and D,L-2-methylsuccinamic acid analogues, J CARB CHEM, 20(1), 2001, pp. 45-55
Citations number
24
Categorie Soggetti
Chemistry & Analysis
Journal title
JOURNAL OF CARBOHYDRATE CHEMISTRY
ISSN journal
07328303 → ACNP
Volume
20
Issue
1
Year of publication
2001
Pages
45 - 55
Database
ISI
SICI code
0732-8303(2001)20:1<45:SONA>2.0.ZU;2-M
Abstract
L-Chlorosuccinic anhydride, L-bromosuccinic anhydride, and D,L-methylsuccin ic anhydride react with 2-acetamido-2-deoxy-beta -D-glucopyranosylamine to give varying mixtures of N-4-(beta -GlcNAc)-2-substituted- and N-4-(beta -G lcNAc)-3-substituted-succinamic acid isomers. The two regioisomers are sepa rated by anion exchange chromatography. The N-4-(beta -GlcNAc)-2-substitute d-succinamic acid isomers are characterized as analogues of N-4-(2-acetamid o-2-deoxy-beta -D-glucopyranosyl)-L-asparagine.