Synthesis of N-aminoacyl-β-glycopyranosylamines — derivatives of natural sialooligosaccharides View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2016-06

AUTHORS

L. M. Likhosherstov, O. S. Novikova, A. M. Sakharov, Z. N. Nysenko, N. G. Kolotyrkina, V. E. Piskarev

ABSTRACT

A synthesis of aminospacered N-β-glycosides of tri-, penta-, hexaand nonasaccharides containing one or two α-D-Neu5Ac residue, namely, α-D-Neu5Ac-(2→6)-β-D-Galp-(1→4)-β-D-Glcp-NHCO(CH2)nNH2 (n = 1 (1d), 3 (1f), 5 (1i)), α-D-Neu5Ac-(2→3)-β-D-Galp-(1→4)β-D-Glcp-NHCO(CH2)nNH2 (n = 1 (2d), 3 (2f), 5 (2i)), β-D-Galp-(1→3)-[α-D-Neu5Ac(2→6)]-β-D-GlcNAcp-(1→3)-β-D-Galp-(1→4)-β-D-Glcp-NHCOCH2NH2 (3d), α-D-Neu5Ac(2→3)-β-D-Galp-(1→3)-[α-D-Neu5Ac-(2→6)]-β-D-GlcNAcp-(1→3)-β-D-Galp-(1→4)-β-DGlcp-NHCOCH2NH2 (4d), α-D-Neu5Ac-(2→3)-β-D-Galp-(1→3)-[α-D-Neu5Ac-(2→6)]-β-D-GlcNAcp-(1→3)-{β-D-Galp-(1→4)-[α-L-Fucp-(1→3)]-β-D-GlcNAcp-(1→6)}-β-D-Galp(1→4)-β-D-Glcp-NHCOCH2NH2 (5d), has been developed. Mono- and disialooligosaccharides from human breast milk and urine treated with ammonium carbamate in aqueous methanol in the presence of NH3 gave the corresponding β-glycopyranosylamines. Their N-acylation with N-hydroxysuccinimidyl esters of N-Z-glycine, N-Z-4-aminobutanoic (GABA) and N-Z-6-aminohexanoic acids (Z is the benzyloxycarbonyl) with subsequent hydrogenolysis of the Z group furnished N-aminoacyl-β-glycopyranosylamines of sialooligosaccharides 1d,f,i, 2d,f,i, 3d—5d in 30—50% yield. More... »

PAGES

1617-1624

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11172-016-1489-6

DOI

http://dx.doi.org/10.1007/s11172-016-1489-6

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1083916294


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