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Synthesis of N-acetyllactosamine containing a d-[6-3H]galactopyranosyl group

✍ Scribed by Nike R. Plessas; Diane A. Blake; Irwin J. Goldstein

Publisher: Elsevier Science
Year: 1984
Tongue: English
Weight: 291 KB
Volume: 129
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(84)85306-9

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✦ Synopsis

A simple and convenient method for the introduction of radiolabel onto C-6' of N-acetyllactosamine is described. 1-N-Benzyl-3-O-beta-D-galactopyranosyl-D-arabinosylamine (1) was synthesized from 3-O-beta-D-galactopyranosyl-D-arabinose as described by Lee and Lee. Compound 1 was oxidized with D-galactose oxidase, and the product reduced with KB3H4 to introduce the label at C-6'. After dilution with unlabeled material, the N-benzyl-3-O-beta-D-[6-3H]galactopyranosyl-D-arabinosylamine was converted into 2-(benzylamino)-2-deoxy-4-O-D-[6-3H]galactopyranosyl-D-glucononitrile , which was subjected to simultaneous hydrogenolysis of the benzylamino and nitrile groups. N-Acetylation of the amino group as described by Alais and Veyrières afforded the crystalline title compound in 63% yield.

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