Synthesis of precursors for the dimeric 3-O-SO3Na Lewis X and Lewis A structures

Carbohydr Res. 1996 Jan 11;280(2):261-76. doi: 10.1016/0008-6215(95)00319-3.

Abstract

Stereoselective syntheses of 3-O-SO3Na-beta-Gal-(1-->4)-beta-GlcNAc- (1-->3)-beta-Gal-(1-->4)-GlcNAc-beta-OBn (15) and 3-O-SO3Na-beta-Gal-(1-->3)-beta-GlcNAc-(1-->3)-beta-Gal-(1-->3)- beta-GlcNAc-(1-->3)-beta-Gal-(1-->4)-Glc-beta-OBn (25) were accomplished through the use of two novel glycosyl donors, namely, ethyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-beta-D- galactopyranosyl)-(1-->4)-3-O-acetyl-2-deoxy-2-phthalimido-1-thio-6-O- trimethylacetyl-beta-D-glucopyranoside (8). and ethyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-beta-D-galactopyranosyl)- (1-->3)-4-O-acetyl-2-deoxy-2-phthalimido-1-thio-6-O-trimethylace tyl-beta-D-glucopyranoside (18).

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • CA-19-9 Antigen
  • Carbohydrate Sequence
  • Fucosyltransferases / metabolism
  • Gangliosides / biosynthesis*
  • Gangliosides / chemistry
  • Glycosylation
  • Lewis Blood Group Antigens / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Molecular Structure
  • Oligosaccharides / biosynthesis*
  • Oligosaccharides / chemistry
  • Sialyl Lewis X Antigen
  • Sialyltransferases / metabolism
  • Sulfotransferases / metabolism

Substances

  • CA-19-9 Antigen
  • Gangliosides
  • Lewis Blood Group Antigens
  • Oligosaccharides
  • Sialyl Lewis X Antigen
  • benzyl O-(3-O-sulfo-galactopyranosyl)-1-3-(2-acetamido-2-deoxyglucopyranosyl)-1-3-galactopyranosyl-1-3-(2-acetamido-2-deoxyglucopyranosyl)-1-3-galactopyranosyl-1-4-glucopyranoside
  • benzyl O-(3-O-sulfogalactopyranosyl)-1-4-(2-acetamido-2-deoxyglucopyranosyl)-1-3-galactopyranosyl-(1-4)-2-acetamido-2-deoxyglucopyranoside
  • sialyl Le(a) ganglioside
  • Fucosyltransferases
  • Sialyltransferases
  • Sulfotransferases