Synthesis of (2S,3R,4R)-3,4-dihydroxyarginine and its inhibitory activity against nitric oxide synthase

Yuichi Masuda, Chitose Maruyama, Kyuichi Kawabata, Yoshimitsu Hamano, Takayuki Doi

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

A synthesis of (2S,3R,4R)-3,4-dihydroxyarginine, a metabolic intermediate of streptothricin, was accomplished. The (3R,4R)-dihydroxy groups were constructed by asymmetric syn-dihydroxylation of (E)-alkene, which was obtained by cross-metathesis of allylamine and L-vinylglycine derivatives. The synthesis of (2S,3S,4S)-3,4-dihydroxyarginine was also achieved in the same manner. The (2S,3R,4R)-3,4-dihydroxyarginine exhibited inhibitory activity against inducible nitric oxide synthase, unlike (2S,3S,4S)-3,4-dihydroxyarginine.

Original languageEnglish
Pages (from-to)5602-5611
Number of pages10
JournalTetrahedron
Volume72
Issue number36
DOIs
Publication statusPublished - 2016

Keywords

  • Asymmetric dihydroxylation
  • Cross metathesis
  • Dihydroxyarginine
  • Nitric oxide synthase

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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