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

(3 R,6 R)-Bis[(1 R,2 S,3 R)-tetrahydroxybutyl)]-2,5-dioxopiperazine (C 12H 22N 2O 11), obtained by cyclization of methyl 2-amino-2-deoxy- d-gluconate, gave orthorhombic crystals with space group C222 1, a = 6.542(1), b = 7.318(1), c = 30.571(3) Å, V = 1463.7(6) Å 3, Z = 4, and D x = 1.61 g.cm −3. Th...

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Bibliographic Details
Published in:Carbohydrate research 1989-04, Vol.187 (2), p.187-195
Main Authors: Perczel, András, Hollósi, Miklós, Császár, János, Fülöp, Vilmos, Kálmán, Alajos, Fasman, Gerald D.
Format: Article
Language:English
Subjects:
Condensed matter: structure, mechanical and thermal properties
Exact sciences and technology
Heterocyclic compounds
Organic compounds
Physics
Structure of solids and liquids
crystallography
Structure of specific crystalline solids
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Summary:(3 R,6 R)-Bis[(1 R,2 S,3 R)-tetrahydroxybutyl)]-2,5-dioxopiperazine (C 12H 22N 2O 11), obtained by cyclization of methyl 2-amino-2-deoxy- d-gluconate, gave orthorhombic crystals with space group C222 1, a = 6.542(1), b = 7.318(1), c = 30.571(3) Å, V = 1463.7(6) Å 3, Z = 4, and D x = 1.61 g.cm −3. The sugar side-chains were linked pseudo equatorially to the dioxopiperazine ring of C 2 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.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(89)80002-3