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Bioorg Med Chem Lett. 2005 Sep 1;15(17):3934-41.

L-arginine analogs as alternate substrates for nitric oxide synthase.

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Department of Chemistry, University of California, Berkeley, CA 94720-1460, USA.


The L-arginine analogs, N(delta)-methyl-L-arginine (deltaMA) and L-canavanine, were used to probe the role of the N delta nitrogen of L-arginine in the reaction catalyzed by nitric oxide synthase (NOS). deltaMA was synthesized and found to be a partial alternate substrate and a weak, reversible inhibitor of NOS with a Ki equal to 1.4 mM. deltaMA undergoes hydroxylation; however, it is not converted further, hence it functions as a partial substrate. L-Canavanine was converted to an L-homoserine presumably via initial hydroxylation and decomposition. The mechanism of this reaction and products of this reaction were not probed further.

[Indexed for MEDLINE]

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