Combined chemical and enzymatic synthesis of the sialylated non reducing terminal sequence of GM1b glycolylated ganglioside, a potential human tumor marker.

N-Glycolylglucosamine 8 was synthesized in 4 steps from anisal glucosamine, via the new crystalline monochloracetyl derivatives 3, 4 and 7. N-Glycolylneuraminic acid 10 was prepared in 59% yield starting from pyruvate and a mixture of 8 and its manno epimer 9 in a 2:3 ratio, with immobilized sialic acid aldolase. Neu5Gc 10 was converted into CMP-NeuGc 11 in the presence of immobilized calf brain CMP-sialate synthetase. Finally 11 was used as a donor in the transfer to the acceptor beta-D-Gal-(1-3)-beta-D-GalNAc-OBn 12 catalyzed by a preparation of porcine liver (2-3)-alpha-sialyltransferase, roughly purified by a chromatography on Cibacron Blue-agarose. alpha-Neu5Gc-(2-3)-beta-D-Gal-(1-3)-beta-D-GalNac-OBn 13 isolated in 56% yield was deprotected to give the non-reducing terminal sequence of GM1b glycolylated ganglioside, which might be expressed in human tumors.
AuthorsA Lubineau, C Augé, C Gautheron-Le Narvor, J C Ginet
JournalBioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 2 Issue 7 Pg. 669-74 (Jul 1994) ISSN: 0968-0896 [Print] ENGLAND
PMID7858974 (Publication Type: Journal Article)
Chemical References
  • Biomarkers, Tumor
  • Enzymes, Immobilized
  • Indicators and Reagents
  • Oligopeptides
  • G(M1) Ganglioside
  • ganglioside M1b
  • Sialyltransferases
  • beta-galactoside alpha-2,3-sialyltransferase
  • N-Acylneuraminate Cytidylyltransferase
  • Fructose-Bisphosphate Aldolase
  • Animals
  • Biomarkers, Tumor
  • Brain (enzymology)
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Cattle
  • Chromatography, Affinity
  • Enzymes, Immobilized
  • Fructose-Bisphosphate Aldolase
  • G(M1) Ganglioside (analogs & derivatives, chemical synthesis, chemistry)
  • Humans
  • Indicators and Reagents
  • Liver (enzymology)
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • N-Acylneuraminate Cytidylyltransferase
  • Neoplasms (metabolism)
  • Oligopeptides (chemical synthesis, chemistry)
  • Optical Rotation
  • Sialyltransferases (isolation & purification)
  • Swine

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