Structure and conformation of 5′-chloro-5′-deoxyarabinosylcytosine: X-ray, 1H and 13C nmr analyses
- 1 May 1988
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 66 (5) , 1203-1208
- https://doi.org/10.1139/v88-197
Abstract
Crystals of 5''-chlorarabinosylcytosine, an inhibitor of nucleic acid synthesis, belong to the orthorhombic space group P212121, and the cell dimensions are a = 6,801(1), b = 9.698(2) and c = 16.497(3) .ANG.. X-ray intensity data were measured on a diffractometer and the structure was determined by direct methods. Least-squares refinement, which included all hydrogen atoms, converged at R = 0.032 for 1251 observed reflections. The conformations about the glycosyl bond is anti, the furanose ring adopts a C3'' endo/C4'' exo pucker and the conformation of the side chain is gauche+, stabilized by an intramolecular C6.sbd.H.cntdot..cntdot..cntdot.C15'' hydrogen bond. 1H and 13C nmr spectra confirm the anti conformation about the glycosyl bond. In D2O solution there is an approximately equal population of N- and S-type conformers of the furanose ring and a trans > gauche+ > gauche- distribution of the 5''-CH2Cl side chain rotamers.This publication has 8 references indexed in Scilit:
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