Synthesis of N-(N-bromoacetylglycyl)-β-D-glycopyranosylamines, derivatives of monoand di-α-L-fucosylated diand trisaccharides View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2017-04

AUTHORS

L. M. Likhosherstov, O. S. Novikova, N. G. Kolotyrkina, B. B. Berezin, V. E. Piskarev

ABSTRACT

N-(N-Bromoacetylglycyl)-β-glycopyranosylamines of diand trisaccharides, namely, α-LFucp-(1→6)-β-D-GlcNAcp-NHCOCH2NHCOCH2Br, α-L-Fucp-(1→3)-β-D-GlcNAcpNHCOCH2NHCOCH2Br, α-L-Fucp-(1→6)-[α-L-Fucp-(1→3)]-β-D-GlcNAcp-NHCOCH2NHCOCH2Br, α-L-Fucp-(1→4)-[β-D-Galp-(1→3)]-β-D-GlcNAcp-NHCOCH2NHCOCH2Br, and α-L-Fucp-(1→2)-β-D-Galp-(1→4)-β-D-Glcp-NHCOCH2NHCOCH2Br, were synthesized in ~70% yields by treatment of the appropriate N-glycyl-β-glycopyranosylamines with N-bromoacetoxysuccinimide in aqueous DMF. The synthesized diand trisaccharide bromo derivatives are proposed for the obtaining of neoglycoconjugates of physiologically active substances, for instance, of daunorubicin anticancer agent.

PAGES

717-720

References to SciGraph publications

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  • 2004-03. An improved procedure for the synthesis of N-bromoacetyl-β-glycopyranosylamines, derivatives of mono- and disaccharides in RUSSIAN CHEMICAL BULLETIN
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  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1007/s11172-017-1798-4

    DOI

    http://dx.doi.org/10.1007/s11172-017-1798-4

    DIMENSIONS

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