Abstract
A simple and convenient method for the introduction of radiolabel onto C-6′ of N-acetyllactosamine is described. 1- N-Benzyl-3- O-β- d-galactopyranosyl- d-arabinosylamine ( 1) was synthesized from 3- O-β- d-galactopyranosyl- d-arabinose as described by Lee and Lee. Compound 1 was oxidized with d-galactose oxidase, and the product reduced with KB 3H 4 to introduce the label at C-6′. After dilution with unlabeled material, the N-benzyl-3- O-β- 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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