Synthesis of sialyllactosamine clusters using carbosilane as core scaffolds by means of chemical and enzymatic approaches

Bioorg Med Chem Lett. 2010 Aug 15;20(16):4906-10. doi: 10.1016/j.bmcl.2010.06.066. Epub 2010 Jun 17.

Abstract

An efficient synthesis of sialyllactosamine (SiaLacNAc) clusters using carbosilanes as core scaffolds has been accomplished by means of chemical and enzymatic approaches. N-Acetyl-D-glucosamine (GlcNAc) clusters having O-glycosidic linkage or S-glycosidic linkage were chemically synthesized from known intermediates in high yields. The GlcNAc clusters were first used as substrates for beta1,4 galactosyl transferase using UDP-galactose (UDP-Gal) as a sugar source to provide corresponding N-acetyllactosamine clusters. Further sugar elongation of the LacNAc clusters was demonstrated using alpha2,3 sialyl transferase and CMP-neuraminic acid (CMP-NANA) to yield the corresponding SiaLacNAc clusters.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylglucosamine / biosynthesis
  • Acetylglucosamine / chemistry
  • Amino Sugars / biosynthesis
  • Amino Sugars / chemistry*
  • Amino Sugars / metabolism
  • Animals
  • Carbohydrate Sequence
  • Cattle
  • N-Acetyllactosamine Synthase / metabolism
  • Rats
  • Silanes / chemistry*
  • Uridine Diphosphate Galactose / chemistry

Substances

  • Amino Sugars
  • Silanes
  • carbosilane
  • lactosamine
  • Uridine Diphosphate Galactose
  • N-acetyllactosamine
  • N-Acetyllactosamine Synthase
  • Acetylglucosamine