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The crystal structure and absolute configuration of 2'-deoxycytidine hydrochloride

Subramanian, E. and Hunter, D. J. (1970) The crystal structure and absolute configuration of 2'-deoxycytidine hydrochloride. Acta crystallographica. Section B, Structural crystallography and crystal chemistry, 26 (4). pp. 303-311. ISSN 0567-7408. https://resolver.caltech.edu/CaltechAUTHORS:20161005-151128064

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Abstract

2'-Deoxycytidine hydrochloride (C_9H_(14)N_3Q_4Cl) was crystallized from water as monoclinic needles, space group P2_1, with ɑ = 6-561, b= 17·659, c=5·125 Å, β = 108·08° and two molecules per cell. The crystal structure has been determined by a three-dimensional X-ray diffraction analysis. A complete hemisphere of data (positive and negative values of both hand k) was collected with a General Electric XRD-5 automatic diffractometer and nickel-filtered Cu Kɑ radiation. The structure was solved by the heavy-atom method. Full-matrix least-squares refinement of both the D and L enantiomorphs has led to respective R values of 0·035 and 0·061; the configuration that gave the lower R value confirms previous conclusions regarding the absolute configuration of the D sugar. The atoms in the pyrimidine ring exhibit small but significant deviations from planarity. The torsion angle describing the conformation about the glycosidic bond is 0°. The least-squares planes through any four ring atoms of the sugar residue, normally used to describe its conformation, are unsatisfactory in that the deviations of the atoms from the planes are rather large. The conformation can, perhaps, be best described relative to the plane through C(l'), C(4'), and 0(1'), with respect to which C(3') is displaced endo by 0·361 Å and C(2') is 0·245 Å exo.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1107/S0567740870002315DOIArticle
http://scripts.iucr.org/cgi-bin/paper?a07341PublisherArticle
Additional Information:© 1970 International Union of Crystallography. Received 31 December 1968. This work was supported in part by research grant No. HE-02143 from the National Heart Institute, U.S. Public Health Service to the California Institute of Technology. We are grateful to Dr R. E. Marsh for helpful discussion and to Mrs J. Westphal for adapting certain computer programs to deal with the anomalous dispersion effect.
Funders:
Funding AgencyGrant Number
NIHHE-02143
U.S. Public Health Service (USPHS)UNSPECIFIED
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Other Numbering System NameOther Numbering System ID
Arthur Amos Noyes Laboratory of Chemical Physics3607
Issue or Number:4
Record Number:CaltechAUTHORS:20161005-151128064
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20161005-151128064
Official Citation:The crystal structure and absolute configuration of 2'-deoxycytidine hydrochloride E. Subramanian and D. J. Hunt Acta Cryst. (1970). B26, 303-311 doi: 10.1107/S0567740870002315
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:70887
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:05 Oct 2016 22:40
Last Modified:03 Oct 2019 16:02

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