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Title: Structures of 1-(2,3-dideoxy-erythro-alpha-D-hexopyranosyl)thymine and the 1-(2,3-dideoxy-erythro-beta-D-hexopyranosyl)thymine. Dioxane complex
Authors: De Winter, Hl ×
Blaton, Norbert
Peeters, Oswald
De Ranter, Camiel
Van Aerschot, Arthur
Herdewijn, Piet #
Issue Date: Apr-1991
Publisher: Munksgaard int publ ltd
Series Title: Acta crystallographica section c-crystal structure communications vol:47 pages:838-842
Abstract: (1) 1-(2,3-Dideoxy-erythro-alpha-D-hexopyranosyl)thymine, C11H16N2O5, M(r) = 256.26, orthorhombic, P2(1)2(1)2(1), a = 4.871 (2), b = 13.182 (7), c = 18.678 (9) angstrom, V = 1199 (1) angstrom3, Z = 4, D(m) = 1.43, D(x) = 1.419 Mg m-3, lambda-(Mo K-alpha) = 0.71069 angstrom, mu = 0.106 mm-1, F(000) = 544, room temperature, final R = 0.032 for 1197 unique observed [F greater-than-or-equal-to 4-sigma(F)] reflections. (II) 1-(2,3-Dideoxy-erythro-beta-D-hexopyranosyl)thymine.dioxane complex, C11H16N2O5.-C4H8O2, M(r) = 344.36, monoclinic, C2, a = 17.23 (1), b = 7.651 (4), c = 13.401 (8) angstrom, beta = 101.14 (5)-degrees, V = 1734 (2) angstrom3, Z = 4, D(m) = 1.32, D(x) = 1.320 Mg m-3, lambda-(Mo K-alpha) = 0.71069 angstrom, mu = 0.098 mm-1, F(000) = 736, room temperature, final R = 0.048 for 1704 unique observed [F greater-than-or-equal-to 4-sigma(F)] reflections. In both structures the pyranose ring adopts a chair conformation flattened at the C(4') and C(1') apex for (I) and (II) respectively. For compound (I), with an intramolecular hydrogen bond between O(55')-H(1) and O(2), the H(1)-O(55')-C(55')-C(5') torsion angle is - sc (synclinal), while in compound (II), where no intramolecular hydrogen bonds are present, this torsion angle is in a + sc orientation. The N-glycosidic torsion angle chi is + sc and - ac (anticlinal) for (I) and (II) respectively. The dioxane molecule in (II) is suspected to be disordered. The packing of both crystals is determined by intermolecular hydrogen bonds. The conformational parameters are in accordance with the IUPAC-IUB Joint Commission on Biochemical Nomenclature [Pure Appl. Chem. (1983), 55, 1273-1280] guidelines.
ISSN: 0108-2701
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
Biocrystallography
× corresponding author
# (joint) last author

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