Combined chemical and enzymatic synthesis of the sialylated non reducing terminal sequence of GM1b glycolylated ganglioside, a potential human tumor marker
✍ Scribed by André Lubineau; Claudine Augé; Christine Gautheron-Le Narvor; Jean-Claude Ginet
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- English
- Weight
- 866 KB
- Volume
- 2
- Category
- Article
- ISSN
- 0968-0896
No coin nor oath required. For personal study only.
✦ Synopsis
Abstrnct--WGlycoly&cossmine 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 immobilii sialic acid aldolase. Net&c 10 was converted into CMP-NeuGc 11 in the presence of immobilii calf brain CMP-sialate synthetase. Finally 11 was used ss a donor in the transfer to the acceptor p-D-Gal-( l-3)-PD-GalNAc-OBn 12 catalyzed by a preparation of porcine liver (2-3)-a-sialyltransferase, roughly purified by a chromatography on Cibacron Blue-agamse. a-Neu5Gc-(2-3)-b&Gal-(l-3)-P-DGalNAc-OBn 13 isolated in 56 4% yield was &protected to give the nonreducing terminal sequence of GM,u glycolylated ganglioside, which might be expressed in human tumors.