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Synthesis of methyl O-(2-O-methyl-β-d-galactopyranosyl)-(1 → 4)-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1 → 3)- β-d-galactopyranoside and 4-nitrophenyl O-β-d-galactopyranosyl-(1 → 4)-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1 → 3)-β-d-galactopyranoside

✍ Scribed by Shaheer H. Khan; Rakesh K. Jain; Khushi L. Matta

Publisher
Elsevier Science
Year
1990
Tongue
English
Weight
704 KB
Volume
203
Category
Article
ISSN
0008-6215

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✦ Synopsis

Recent years have seen a remarkable surge of interest in the study of U-Lfucosyltransferases.

Of these L-fucosyltransferases, the enzyme (143)~a+fucosyltransferase has attracted a great deal of clinical interest as a potential tumor marker. This enzyme catalyzes the transfer of an L-fucosyl group from GDP-L-fucose to O-3 of 2-acetamido-2-deoxy-D-glucose or D-glucose, and exhibits a strict specificity for acceptors having the nonreducing terminal sequence P-D-Galp-( 1 +4)-D-GlcpNAc or -D-(Gl~p)~. In recent studies, it was suggested that this enzyme is responsible for the unusually high accumulation of polyfucosylated, repeated N-acetyllactosamine chains that are found as part of glycolipids in a variety of human cancers3.

Based on specificity for different acceptor-substrates and differences in biochemical properties between enzymes from different sources, at least seven (1-+3)-a-Lfucosyltransferases are known4. To simplify the assay procedures for the specific quantitative determination of individual L-fucosyltransferases, we have embarked on a synthetic program to obtain compounds capable of acting as acceptors for a single enzyme, even in the presence of other, related enzymes. We have recently successfully applied this approach to the assay of (l-+3)-a-L-fucosyltransferase from human serum5 by use of our synthetic acceptor substrate, 2-acetamido-2-deoxy-4-0-(20methyl-@-D-galactopyranosyl)-D-glucopyranoside

(2'-O-methyl-N-acetyllactosamine)5~6. This same compound has also proven to be an excellent instrument in a number of clinical * Synthetic Studies in Carbohydrates, Part LXIX. For Part LXVIII, see ref. I.

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