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JBC, Vol. 253, Issue 14, 4907-4910, Jul, 1978
N. J. Oppenheimer
The products of the choleragen-catalyzed reaction of NAD+ with guanidine
HCl or L-arginine have been isolated by high performance liquid
chromatography. Analysis of 1H NMR spectra obtained at 360 MHz establishes
the structure of the isolated products to be adenosine diphosphoribosyl
guanidiniums present as 1:1 mixtures of alpha and beta anomeric forms.
Direct observation of the choleragen-catalyzed reaction of NAD+ with
L-arginine by 1H NMR spectroscopy establishes that choleragen synthesizes
an alpha anomeric linkage that is subject to subsequent anomerization. The
stereospecificity of the reaction provides further evidence that choleragen
behaves as an enzyme and may be related mechanistically to other
ADP-ribosyltransferases.
Structural determination and stereospecificity of the choleragen-catalyzed reaction of NAD+ with guanidines
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