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Published July 28, 1978 | public
Journal Article

Differential Rates of Proton Exchange for the Guanidinium Nitrogens of L-Arginine Determined by Natural-Abundance Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy

Abstract

Differential rates of N-H proton-exchange reactions have been determined for the guanidinium nitrogens of l-arginine, 1̂, in the pH range of 0.5 to 11.5 by natural-abundance nitrogen-15 NMR spectroscopy. Base-catalyzed N-H proton exchange of the -NH- group is found to be two times faster than for the guanidino -NH_2 groups. The results can be rationalized by consideration of the contributions of various valence-bond structures to the resonance hybrid of 1.

Additional Information

© 1978 Academic Press, Inc. Received May 26, 1978. Supported by the Public Health Service, Research Grant No. GM-11072 from the Division of General Medical Sciences, and by the National Science Foundation.

Additional details

Created:
August 19, 2023
Modified:
October 25, 2023