The first bovine beta 1,4-galactosyltransferase reaction with an acyclic acceptor substrate, 3-acetamido-1,2-propanediol, to yield a 3-O-beta-D-galactopyranosyl-sn-glycerol skeleton

Org Lett. 2001 Jan 11;3(1):1-3. doi: 10.1021/ol006590n.

Abstract

[figure: see text] Reactivity of bovine beta 1,4-galactosyltransferase was examined for a series of acyclic acceptor substrates both in the presence and the absence of alpha-lactalbumin (alpha-La). It was found that this enzyme could utilize (R)-3-acetamido-1,2-propanediol (1) as an acceptor substrate regardless of the cofactor protein. The product was determined to be 1-O-beta-D-galactopyranosyl-(R)-3-acetamido-1,2-propanediol (2). Glycerol without the acetamido group was inactive, indicating that this functional group plays a key role in the enzyme reaction.

MeSH terms

  • Animals
  • Catalysis
  • Cattle
  • Galactosides / chemistry
  • Lactalbumin / metabolism
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Monosaccharides / metabolism
  • N-Acetyllactosamine Synthase / metabolism*
  • Propylene Glycols / chemistry
  • Propylene Glycols / metabolism*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Substrate Specificity

Substances

  • 1-O-galactopyranosyl-3-acetamido-1,2-propanediol
  • 3-acetamido-1,2-propanediol
  • Galactosides
  • Monosaccharides
  • Propylene Glycols
  • Lactalbumin
  • N-Acetyllactosamine Synthase