Synthesis of oligosaccharides related to HNK-1 antigen, part 3 - Synthesis of 3-O-sulfoglucuronyl lacto-N-neotetraose 2-aminoethyl glycoside and biotinylated neoglycoconjugates thereof

• Published in: Carbohydrate research Vol. 329; no. 4; pp. 717 - 730
• Main Authors: Kornilov, AV, Sherman, AA, Kononov, LO, Shashkov, AS, Nifant'ev, NE
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier 01.12.2000
• Subjects: Biochemistry & Molecular Biology; Chemistry; Chemistry, Applied; Chemistry, Organic; Life Sciences & Biomedicine; Physical Sciences; Science & Technology; NERVOUS-SYSTEM; HNK-1; OLIGOSACCHARIDES; HNK-1 ANTIGEN; glucuronic acid; lactonization; CELL-ADHESION MOLECULES; neoglycoconjugates; GLYCOLIPIDS
• ISSN: 0008-6215
• DOI: 10.1016/S0008-6215(00)00258-5

The 2-aminoethyl glycoside of pentasaccharide 3-O-sulfo-GlcA(beta -1 --> 3)Gal(beta -1 --> 4)GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta (1) and its conjugates with biotin and biotinylated polyacrylic acid were synthesized as molecular probes to investigate the recognition of the HNK-1 epitope containing carbohydrates by proteins. Key steps in the first of two investigated schemes for the preparation of the target compound 1 were (a) assembling of the pentasaccharide backbone (compound 10) by glycosylation of selectively substituted allyl glycoside of the trisaccharide GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta with glucuronyl-galactose glycosyl donor, (b) transformation of the allyl aglycon in 10 into 2-azidoethyl one (to give 11), (c) selective deprotection of the OH group at C-3 of the GlcA residue in 11 via saponification, intramolecular formation of 6,3-lacton (13) and its methanolysis, and (d) subsequent O-sulfation. The alternative scheme with the use of 2-azido-ethyl glycoside of the trisaccharide GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta instead of the allyl glycoside 6 was less effective due to smaller yield at the step of pentasaccharide synthesis. Additionally to 1 the 2-aminoethyl glycosides of the oligosaccharides GlcA(beta -1 --> 3)Gal(beta -1 --> 4)GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta, 3-O-sulfo-GlcA(beta -1 --> 3)Gal(beta, and GlcA(beta -1 --> 3)Gal(beta were also synthesized. (C) 2000 Elsevier Science Ltd. All rights reserved.