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L-arginine analogs as alternate substrates for nitric oxide synthase

Academic Article
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Overview

authors

  • Luzzi, S. D.
  • Marletta, Michael

publication date

  • September 2005

journal

  • Bioorganic & Medicinal Chemistry Letters  Journal

abstract

  • 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.

subject areas

  • Arginine
  • Biotransformation
  • Chromatography, High Pressure Liquid
  • Enzyme Inhibitors
  • Humans
  • Kinetics
  • Nitric Oxide Synthase
  • Nitric Oxide Synthase Type II
  • Structure-Activity Relationship
  • Substrate Specificity
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Research

keywords

  • arginine
  • canavanine
  • nitric oxide synthase
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Identity

International Standard Serial Number (ISSN)

  • 0960-894X

Digital Object Identifier (DOI)

  • 10.1016/j.bmcl.2005.05.088

PubMed ID

  • 15993059
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Additional Document Info

start page

  • 3934

end page

  • 3941

volume

  • 15

issue

  • 17

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