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A nitrogen-15 NMR study of the barriers to isomerization about guanidinium and guanidino carbon-nitrogen bonds in L-arginine

Kanamori, Keiko and Roberts, John D. (1983) A nitrogen-15 NMR study of the barriers to isomerization about guanidinium and guanidino carbon-nitrogen bonds in L-arginine. Journal of the American Chemical Society, 105 (14). pp. 4698-4701. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151005-090619934

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Abstract

^(15)N nuclear magnetic resonance (NMR) spectroscopy has been employed to investigate barriers to isomerization about the C-N2 bond in guanidinium and guanidino groups of L-arginine by line-shape analyses of the N1 and N3 resonances in a 50% (v/v) dimethyl sulfoxide/water solution from -52 to 25 ºC. The free energies of activation were found to be 12.9 and 10.4 kcal/mol, and the chemical-shift differences between the nonequivalent nitrogens, N1 and N3, were 2.4 and 42.3 ppm for the guanidinium and guanidino groups of L-arginine, respectively. For the guanidino form of L-arginine, the three possible tautomers with different arrangements of the guanidino protons are interconverted rapidly on the NMR time scale over the whole of the temperature range studied. Approximately one-third of the guanidino form is present as the R-N=C(NH_2)_2 tautomer. The results are compared with those previously reported for tetramethylguanidine derivatives.


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URLURL TypeDescription
http://dx.doi.org/10.1021/ja00352a028DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00352a028PublisherArticle
Additional Information:© 1983 American Chemical Society. Received December 13, 1982. Supported by the National Science Foundation, and by the US. Public Health Service, Grant No. GM-11072 from the Division of General Medical Sciences. We are pleased to acknowledge use of the Southern California Regional NMR Center facilities (Bruker WM-500 spectrometer) supported by National Science Foundation Grant CHE79-16324.
Funders:
Funding AgencyGrant Number
U.S. Public Health Service (USPHS)GM-11072
NSFCHE79-16324
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Caltech Gates and Crellin Laboratories of Chemistry6773
Record Number:CaltechAUTHORS:20151005-090619934
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151005-090619934
Official Citation:A nitrogen-15 NMR study of the barriers to isomerization about guanidinium and guanidino carbon-nitrogen bonds in L-arginine Keiko Kanamori and John D. Roberts Journal of the American Chemical Society 1983 105 (14), 4698-4701 DOI: 10.1021/ja00352a028
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60748
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:05 Oct 2015 18:40
Last Modified:05 Oct 2015 18:40

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