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Nucleosides, Nucleotides & Nucleic Acids Volume 20, 2001 - Issue 8
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Original Articles

NMR STUDIES AND SEMI-EMPIRICAL ENERGY CALCULATIONS FOR CYCLIC ADP-RIBOSE

Trevor J. Rutherford School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT, UKCorrespondence[email protected]
,
John Wilkie School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT, UK
,
Chinh Q. Vu Division of Pharmaceutical Sciences, College of Pharmacy and Lucille P. Markey Cancer Center, University of Kentucky, Lexington, KY, 40506, U.S.A.
,
Klaus D. Schnackerz School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT, UK
,
Myron K. Jacobson Division of Pharmaceutical Sciences, College of Pharmacy and Lucille P. Markey Cancer Center, University of Kentucky, Lexington, KY, 40506, U.S.A.
&
David Gani School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT, UK
Pages 1485-1495 | Received 20 Jun 2000, Accepted 30 Dec 2000, Published online: 17 Aug 2006
 
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Abstract

A possible pH-dependent conformational switch was investigated for cyclic ADP-ribose. NMR signals for the exchangeable protons were observed in H2O at low temperature, but there was no direct evidence for the protonation of N-3 at neutral pH that has previously been postulated. MNDO calculations indicated that pH dependent 31P chemical shift changes are attributable to protonation of the phosphate adjacent to the N-1 of adenine, and not due to trans-annular hydrogen bonding with a protonated N-3.

ACKNOWLEDGMENTS

This study was supported in part by NIH grant NS38496 and by a Welcome Trust grant 040331.

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