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Studies of tautomers and protonation of adenine and its derivatives by nitrogen-15 nuclear magnetic resonance spectroscopy

Gonnella, Nina C. and Nakanishi, Hiroshi and Holtwick, Joseph B. and Horowitz, David S. and Kanamori, Keiko and Leonard, Nelson J. and Roberts, John D. (1983) Studies of tautomers and protonation of adenine and its derivatives by nitrogen-15 nuclear magnetic resonance spectroscopy. Journal of the American Chemical Society, 105 (7). pp. 2050-2055. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151005-090620758

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Abstract

High-resolution nitrogen-15 NMR spectra of adenine have been obtained both at the S-adenosylmethionine level and for a uniformly enriched sample prepared from S-adenosylmethionine isolated from yeast grown with ^(15)NH_4CI as the principal nitrogen source. Specific ^(15)N labeling at N1, N3, N6’, N7, and N9 provided unequivocal assignments of the chemical shifts as well as elucidation of the position of the tautomeric equilibrium. For comparison, the nitrogen resonances of several adenine derivatives were determined at the natural-abundance level. The protonation sites of many of these substances were determined from the effect of pH on the nitrogen chemical shifts. Both adenine and its conjugate acid clearly exist as the N9-H tautomers in aqueous solution. Conversion of adenine to its conjugate base (pK, ~ 10) results in a 56 ppm downfield shift of the N9 resonance.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja00345a063DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00345a063PublisherArticle
Additional Information:© 1983 American Chemical Society. Received March 26, 1982. Supported by the National Science Foundation (CHE 7904262) and by the Public Health Service Grant GM-11072 from the Division of General Medical Sciences; the work performed at the University of Illinois was supported by the National Science Foundation (CHE 7922001).
Funders:
Funding AgencyGrant Number
NSFCHE 7904262
U.S. Public Health Service (USPHS)GM-11072
NSFCHE 7922001
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Caltech Gates and Crellin Laboratories of Chemistry6377
Record Number:CaltechAUTHORS:20151005-090620758
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151005-090620758
Official Citation:Studies of tautomers and protonation of adenine and its derivatives by nitrogen-15 nuclear magnetic resonance spectroscopy Nina C. Gonnella, Hiroshi Nakanishi, Joseph B. Holtwick, David S. Horowitz, Keiko Kanamori, Nelson J. Leonard, and John D. Roberts Journal of the American Chemical Society 1983 105 (7), 2050-2055 DOI: 10.1021/ja00345a063
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60751
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:05 Oct 2015 18:30
Last Modified:20 Sep 2016 20:56

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