Synthesis of N-aminoacyl-β-glycopyranosylamines — derivatives of natural sialooligosaccharides

Synthesis of N-aminoacyl-β-glycopyranosylamines — derivatives of natural sialooligosaccharides Научная публикация

Журнал

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Вых. Данные

Год: 2016, Том: 65, Номер: 6, Страницы: 1617-1624 Страниц : 8 DOI: 10.1007/s11172-016-1489-6

Авторы

Likhosherstov L.M. ¹ , Novikova O.S. ¹ , Sakharov A.M. ¹ , Nysenko Z.N. ¹ , Kolotyrkina N.G. ¹ , Piskarev V.E. ²

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

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) n NH2 (n = 1 (1d), 3 (1f), 5 (1i)), α-D-Neu5Ac-(2→3)-β-D-Galp-(1→4)β-D-Glcp-NHCO(CH2) n NH2 (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.

Likhosherstov L.M. , Novikova O.S. , Sakharov A.M. , Nysenko Z.N. , Kolotyrkina N.G. , Piskarev V.E.
Synthesis of N-aminoacyl-β-glycopyranosylamines — derivatives of natural sialooligosaccharides
Russian Chemical Bulletin. 2016. V.65. N6. P.1617-1624. DOI: 10.1007/s11172-016-1489-6 WOS Scopus OpenAlex

≡ Web of science:	WOS:000395522500022
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