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J Med Chem. 1994 Apr 1;37(7):885-7.

Synthesis of L-thiocitrulline, L-homothiocitrulline, and S-methyl-L-thiocitrulline: a new class of potent nitric oxide synthase inhibitors.

Author information

1
Department of Biochemistry, Medical College of Wisconsin, Milwaukee 53226.

Abstract

Nitric oxide synthase catalyzes the NADPH- and O2-dependent conversion of L-arginine to L-citrulline and nitric oxide. L-Thiocitrulline, L-homothiocitrulline, and S-methyl-L-thiocitrulline, novel citrulline analogs, have been synthesized and are shown to be potent inhibitors of both the constitutive brain and the inducible smooth muscle isoforms of nitric oxide synthase. Although many N omega-monosubstituted arginine derivatives inhibit nitric oxide synthase, inhibitory citrulline derivatives have not previously been reported. S-Methyl-L-thiocitrulline is significantly more potent than N omega-methyl-L-arginine, the prototypic nitric oxide synthase inhibitor.

PMID:
7512141
DOI:
10.1021/jm00033a004
[Indexed for MEDLINE]

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