Synthesis of (2S, 3R, 4R)-3, 4-dihydroxyarginine and its inhibitory activity against nitric oxide synthase. Issue 36 (8th September 2016)

• Record Type: Journal Article
• Authors: Masuda, Yuichi; Maruyama, Chitose; Kawabata, Kyuichi; Hamano, Yoshimitsu; Doi, Takayuki
• Is Part Of: Tetrahedron. Volume 72:Issue 36(2016)
• Page Start: 5602
• Page End: 5611
• Publication Date: 2016-09-08
• Subjects: Dihydroxyarginine -- Cross metathesis -- Asymmetric dihydroxylation -- Nitric oxide synthase; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.07.050
• Languages: English
• ISSNs: 0040-4020

Abstract

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