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Molecular Pharmacology

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Research ArticleArticle

Structural Requirements for Activity of Nucleosides as Substrates for Adenosine Kinase: Orientation of Substituents on the Pentofuranosyl Ring

L. LEE BENNETT JR. and DONALD L. HILL
Molecular Pharmacology November 1975, 11 (6) 803-808;
L. LEE BENNETT JR.
Kettering-Meyer Laboratory, Southern Research Institute, Birmingham, Alabama 35205
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DONALD L. HILL
Kettering-Meyer Laboratory, Southern Research Institute, Birmingham, Alabama 35205
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Abstract

Selected nucleosides of adenine and 8-azaadenine were examined as substrates for adenosine kinase (EC 2.7.1.20), an enzyme that catalyzes the phosphorylation of many biologically active nucleosides, to evaluate the effects on substrate activity of various orientations of substituents on the pentofuranosyl ring. The enzyme used was partially purified from cultured H.Ep.2 cells. Although not all the possible isomers were studied, the results, together with other reported findings, lead to the conclusion that necessary, but not sufficient, conditions for substrate activity are the following: (a) the nucleoside should have a 2'-hydroxy group, (b) the 2'-hydroxy group should be trans to the purine moiety, and (c) there should exist a considerable degree of freedom of rotation about the C-1'—N-9 bond. If these conditions are met, the 3'-hydroxy group and the 4'-hydroxymethyl group may be either cis or trans to the purine ring. These results add to understanding of the mode of binding of substrates to adenosine kinase and should aid in the design of new nucleoside analogues as growth-inhibitory on antitumor agents.

ACKNOWLEDGMENTS We thank Dr. J. A. Montgomery, Dr. Y. F. Shealy, and Ms. H. J. Thomas for provision of compounds.

  • Copyright ©, 1975, by Academic Press, Inc.

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Molecular Pharmacology
Vol. 11, Issue 6
1 Nov 1975
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Research ArticleArticle

Structural Requirements for Activity of Nucleosides as Substrates for Adenosine Kinase: Orientation of Substituents on the Pentofuranosyl Ring

L. LEE BENNETT and DONALD L. HILL
Molecular Pharmacology November 1, 1975, 11 (6) 803-808;

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Research ArticleArticle

Structural Requirements for Activity of Nucleosides as Substrates for Adenosine Kinase: Orientation of Substituents on the Pentofuranosyl Ring

L. LEE BENNETT and DONALD L. HILL
Molecular Pharmacology November 1, 1975, 11 (6) 803-808;
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