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

Abstract	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.
Authors	A Lubineau, C Augé, C Gautheron-Le Narvor, J C Ginet
Journal	Bioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 2 Issue 7 Pg. 669-74 (Jul 1994) ISSN: 0968-0896 [Print] England
PMID	7858974 (Publication Type: Journal Article)
Chemical References	Biomarkers, Tumor Enzymes, Immobilized Indicators and Reagents Oligopeptides G(M1) Ganglioside ganglioside M1b Sialyltransferases N-Acylneuraminate Cytidylyltransferase Fructose-Bisphosphate Aldolase beta-Galactoside alpha-2,3-Sialyltransferase
Topics	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 beta-Galactoside alpha-2,3-Sialyltransferase

Join CureHunter, for free Research Interface BASIC access!

Take advantage of free CureHunter research engine access to explore the best drug and treatment options for any disease. Find out why thousands of doctors, pharma researchers and patient activists around the world use CureHunter every day.

Realize the full power of the drug-disease research graph!