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Chemical synthesis and kinetic characterization of UDP-2-deoxy-d-lyxo-hexose(“UDP-2-deoxy-d-galactose”), a donor-substrate for β-(1 → 4)-d-galactosyltransferase

✍ Scribed by Geeta Srivastava; Ole Hindsgaul; Monica M. Palcic

Publisher
Elsevier Science
Year
1993
Tongue
English
Weight
578 KB
Volume
245
Category
Article
ISSN
0008-6215

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✦ Synopsis

Bovine p-(1 + 4kgalactosyltransferase

(GalT) transfers galactose from UDP-galactose to B-D-GlcpNAc-terminating oligosaccharides to produce N-acetyllactosamine sequences. We report here the chemical synthesis, structural characterization and enzymatic evaluation of the very labile UDP-Zdeoxy-D-lyxo-hexose ("UDP-2-deoxy-galactose,"

  1. as an alternate donor for GalT. Donor 2 had kinetic parameters, including a K, value of 51 PM, almost identical to those for the natural substrate UDP-galactose when /3-p-GlcpNAc-G(CH,),CGGMe was used as the acceptor. The product of the enzymatic transfer was isolated and confirmed to have the expected 2'-deoxy-N-acetyllactosamine sequence.

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Synthesis of Protected Hexp-(1 → 4)-β-D-GlcpNAc-(1 → 2)-α-D-Manp-(1 → O)(CH2)7CH3 Sequences (Hex: β-D-Glc, 4-deoxy-4fluoro-β-D-Gal, or 4-deoxy-β-D-Gal) Using a Glc-GlcNPhth Donor, Eventually Fluorinated or Deoxygenated at the Oligosaccharide Level. -The title trisaccharide derivatives are prepared