Treatment of benzyl 2-acetamido-2-deoxy-alpha-D-galactopyranoside with 4-methoxybenzaldehyde dimethyl acetal in N,N-dimethylformamide in the presence of 4-toluenesulfonic acid afforded the 4,6-O-(4-methoxybenzylidene) acetal, which was glycosylated with 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosy
Methyl 3-amino-3-deoxy-β-d-galactopyranosyl-(1 → 4)-2-acetamido-2-deoxy-β-d-glucopyranoside: An inhibitor of UDP-d-galactose: β-d-galactopyranosyl-(1 → 4)-2-acetamido-2-deoxy-d-glucose (1 → 3)-α-d-galactopyranosyltransferase
✍ Scribed by Anne-Charlotte Helland; Ole Hindsgaul; Monica M. Palcic; Cheryl L.M. Stults; Bruce A. Macher
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- English
- Weight
- 422 KB
- Volume
- 276
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
UDP-D-galactose:fl-D-galactopyranosyl-(l ~ 4)-2-acetamido-2-deoxy-D-glucose a-(1 ~ 3)-Dgalactopyranosyltransferase [E.C . 2.4.1.151] transfers o-galactosyl-residues from the sugar nucleotide with retention of configuration. We report here that synthetic methyl 3'-amino-3'-deoxy-N-acetyllactosaminide (9), where the hydroxyl group normally undergoing galactosylation has been replaced by amino group, is an inhibitor for this enzyme with K i = 104/xM. The mode of inhibition is not competitive, but appears to be specific, since other glycosyltransferases were not affected by 9.
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