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

被引：5

作者：

Masuda, Yuichi ^{[1
,2
]}

Maruyama, Chitose ^{[3
]}

Kawabata, Kyuichi ^{[3
]}

Hamano, Yoshimitsu ^{[3
]}

Doi, Takayuki ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, 6-3 Aza Aoba, Sendai, Miyagi 9808578, Japan

[2] Mie Univ, Grad Sch Bioresources, 1577 Kurimamachiya Cho, Tsu, Mie 5148507, Japan

[3] Fukui Prefectural Univ, Dept Biosci, 4-1-1 Matsuoka Kenjojima, Eiheiji Cho, Fukui 9101195, Japan

来源：

TETRAHEDRON | 2016年 / 72卷 / 36期

关键词：

Dihydroxyarginine; Cross metathesis; Asymmetric dihydroxylation; Nitric oxide synthase; STREPTOTHRICIN-F; ASYMMETRIC DIHYDROXYLATION; CHEMICAL-STRUCTURE; SELECTABLE MARKER; NMR-SPECTROSCOPY; GENE DISRUPTION; LIGAND CLASS; AMINO-ACIDS; BIOSYNTHESIS; STREPTOLIDINE;

D O I：

10.1016/j.tet.2016.07.050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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-dhydroxyarginine exhibited inhibitory activity against inducible nitric oxide synthase, unlike (2S,3S,4S)-,4-dihydroxyarginine. (C) 2016 Elsevier Ltd. All rights reserved.

引用

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页码：5602 / 5611

页数：10

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