On the unexpected formation of a new dioxopiperazine containing carbohydrate side-chains: An X-ray study

András Perczel, Miklós Hollósi, János Császár, Vilmos Fülöp, Alajos Kálmán, Gerald D. Fasman

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Abstract

(3R,6R)-Bis[(1R,2S,3R)-tetrahydroxybutyl)]-2,5-dioxopiperazine (C12H22N2O11), obtained by cyclization of methyl 2-amino-2-deoxy-d-gluconate, gave orthorhombic crystals with space group C2221, a = 6.542(1), b = 7.318(1), c = 30.571(3) Å, V = 1463.7(6) Å3, Z = 4, and Dx = 1.61 g.cm-3. The sugar side-chains were linked pseudo equatorially to the dioxopiperazine ring of C2 molecular symmetry and were close packed (packing coefficient, 0.81) via four-fold rings of OH···O hydrogen bonds. Each sugar side-chain participates in eight hydrogen bonds with four neighbouring molecules, which produce closely packed 2-dimensional layers, possibly even in solution.

Original languageEnglish
Pages (from-to)187-195
Number of pages9
JournalCarbohydrate Research
Volume187
Issue number2
DOIs
Publication statusPublished - Apr 15 1989

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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