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

doi:10.1016/j.tet.2016.07.050

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

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

4 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 language	English
Pages (from-to)	5602-5611
Number of pages	10
Journal	Tetrahedron
Volume	72
Issue number	36
DOIs	https://doi.org/10.1016/j.tet.2016.07.050
Publication status	Published - 2016

Keywords

Asymmetric dihydroxylation
Cross metathesis
Dihydroxyarginine
Nitric oxide synthase

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10.1016/j.tet.2016.07.050

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

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.",

keywords = "Asymmetric dihydroxylation, Cross metathesis, Dihydroxyarginine, Nitric oxide synthase",

author = "Yuichi Masuda and Chitose Maruyama and Kyuichi Kawabata and Yoshimitsu Hamano and Takayuki Doi",

note = "Funding Information: This research was supported by a grant for {\textquoteleft}{\textquoteleft}Project Focused on Developing Key Technology for Discovering and Manufacturing Drugs for Next-Generation Treatment and Diagnosis{\textquoteright}{\textquoteright} from Japan Agency for Medical Research and Development (AMED), Japan . We thank Dr. Kazuo Shin-ya (AIST) for technical discussion. Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

year = "2016",

doi = "10.1016/j.tet.2016.07.050",

language = "English",

volume = "72",

pages = "5602--5611",

journal = "Tetrahedron",

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number = "36",

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TY - JOUR

T1 - Synthesis of (2S,3R,4R)-3,4-dihydroxyarginine and its inhibitory activity against nitric oxide synthase

AU - Masuda, Yuichi

AU - Maruyama, Chitose

AU - Kawabata, Kyuichi

AU - Hamano, Yoshimitsu

AU - Doi, Takayuki

N1 - Funding Information: This research was supported by a grant for ‘‘Project Focused on Developing Key Technology for Discovering and Manufacturing Drugs for Next-Generation Treatment and Diagnosis’’ from Japan Agency for Medical Research and Development (AMED), Japan . We thank Dr. Kazuo Shin-ya (AIST) for technical discussion. Publisher Copyright: © 2016 Elsevier Ltd

PY - 2016

Y1 - 2016

N2 - 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.

AB - 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.

KW - Asymmetric dihydroxylation

KW - Cross metathesis

KW - Dihydroxyarginine

KW - Nitric oxide synthase

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U2 - 10.1016/j.tet.2016.07.050

DO - 10.1016/j.tet.2016.07.050

M3 - Article

AN - SCOPUS:84981186518

SN - 0040-4020

VL - 72

SP - 5602

EP - 5611

JO - Tetrahedron

JF - Tetrahedron

IS - 36

ER -

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

Abstract

Keywords

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