Molecular Architecture of the Cephalosporins. Insights into Biological Activity Based on Structural Investigations

Journal of the American Chemical Society

Volumn 92, Issue 18, 1970, Pages 5489-5507

  Sweet, Robert M ^a   Dahl, Lawrence F ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CEPHALOSPORIN DERIVATIVE;

ARTICLE; X RAY DIFFRACTION;

CEPHALOSPORINS; X-RAY DIFFRACTION;

EID: 0014938290     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00721a032     Document Type: Article

References (47)

1. Previous paper reporting preliminary results from this work: R. M. Sweet and L. F. Dahl, Biochem. Biophys. Res. Commun., 34, 14 (1969);
2. presented in part at the Eighth International Congress of the International Union of Crystallography, Buffalo, N. Y., August 8, 1969;
3. see Acta Crystallogr., A, 25, part S3, S201 (1969).
4. This manuscript is based in part on a dissertation submitted by R. M. Sweet to the Graduate School of the University of Wisconsin in partial fulfillment of the requirements for the Ph.D. degree, Jan 1970.
5. D. J. Tipper and J. L. Strominger, Proc. Nat. Acad. Sci., 54, 1133 (1965), and references cited therein.
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13. M. Gorman, Lilly Research Laboratories, Indianapolis, Ind., private communication to R. M. Sweet, 1969.
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15. Alan S. Foust, Ph.D. Thesis, University of Wisconsin, Madison, Wis., 1970.
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18. 2.
19. J. C. Calabrese, “PROGRAM MIRAGE,” University of Wisconsin, Madison, Wis., 1970. The hydrogen atoms were placed in idealized positions to complete the polyhedron about the connected atom at interatomic distances proper for the type of bond (1.07 to 1.10 Å for C-H and N-H bonds).
20. The thiophene ring parameters used in the rigid-body model are those averaged from two independent, precise structural determinations (R. A. Bonham and F. A. Momany, J. Phys. Chem., 67, 2474 (1963));
21. 2v-2 mm point group symmetry. These averaged parameters are: S-C(1) = 1.714 Å, C(1)-C(2) = 1.370 Å, C(2)-C(2′) = 1.421 Å, ≮ C(2)-S-C(2′) = 92°11′, ≮ S-C(1)-C(2) = 111°26′, and ≮ C(1)-C(2)-C(2′) = 112°28.5′.
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33. 2O was determined by titration and nmr measurements; private communication from R. Pfeiffer (Eli Lilly and Co., Indianapolis, Ind.) to R. M. Sweet, 1969.
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41. G. J. Pitt, Acta Crystallogr., 5, 770 (1952).
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44. M. N. G. James, D. Hall, and D. C. Hodgkin, Nature (London), 220, 168 (1968). Molecular parameters were obtained by private communication with Dr. James.
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47. S. Wolfe, J. C. Godfrey, C. T. Holdrege, and Y. G. Perron, Can. J. Chem., 46, 2549 (1968).