Synthesis of a novel N-O-interglycosidic disaccharide

Miklós Hornyák, F. Sztaricskai, István F. Pelyvás, G. Batta

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The carbohydrate subunits carrying an N-O-interglycosidic bond play a very important role in the biological activity of the enediyne antibiotics. Condensation of O-(α- and β-D-glucopyranosyl)hydroxylamine (5a and 5b) with the hex-3-ulopyranoside (6) furnished methyl 4,6-O-benzylidene-2,3-dideoxy-3-(2,3,4,6-tetra-O-benzyl-α-D- glucopyranosyloxy)imino-α- and β-D-erythro-hexopyranoside (7a and 7b). Stereoselective reduction of the C=N bond of 7a and 7b with sodium cyanoborohydride resulted in the formation of the required protected N-O-interglycosidic disaccharides (8a and 8b). Finally, catalytic hydrogenation of 8a afforded methyl 2,3-dideoxy-3-(α-D-glucopyranosyloxy)amino-α-D-ribo- hexopyranoside (9a). Under similar conditions the β anomer 8b underwent decomposition.

Original languageEnglish
Pages (from-to)1787-1792
Number of pages6
JournalCarbohydrate Research
Volume338
Issue number17
DOIs
Publication statusPublished - Aug 12 2003

Fingerprint

Enediynes
Hydroxylamine
Hydrogenation
Disaccharides
Bioactivity
Condensation
Carbohydrates
Anti-Bacterial Agents
Decomposition
sodium cyanoborohydride

Keywords

  • H and C NMR
  • N-O-interglycosidic disaccharide
  • Synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Synthesis of a novel N-O-interglycosidic disaccharide. / Hornyák, Miklós; Sztaricskai, F.; Pelyvás, István F.; Batta, G.

In: Carbohydrate Research, Vol. 338, No. 17, 12.08.2003, p. 1787-1792.

Research output: Contribution to journalArticle

Hornyák, Miklós ; Sztaricskai, F. ; Pelyvás, István F. ; Batta, G. / Synthesis of a novel N-O-interglycosidic disaccharide. In: Carbohydrate Research. 2003 ; Vol. 338, No. 17. pp. 1787-1792.
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