Revision of the structure of raphanusanins, phototropism-regulating substances of radish hypocotyls

Nobuyuki Harada; Hisahiro Hagiwara; Hiroshi Ono; Hisashi Uda; Shigeru Ohba; Mari Kubota; Shigeru Nishiyama; Shosuke Yamamura; Koji Hasegawa; Masako Sakoda

doi:10.1016/S0040-4039(00)93595-0

Revision of the structure of raphanusanins, phototropism-regulating substances of radish hypocotyls

Nobuyuki Harada, Hisahiro Hagiwara, Hiroshi Ono, Hisashi Uda, Shigeru Ohba, Mari Kubota, Shigeru Nishiyama, Shosuke Yamamura, Koji Hasegawa, Masako Sakoda

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

13 Citations (Scopus)

Abstract

The structures of raphanusanins A and B, growth inhibitors involved in phototropism of radish hypocotyls, were determined by X-ray crystallographic structure analysis and by spectral studies to be (3R^*,6R^*)- and (3R^*,6S^*)-3-[methoxy(methylthio)methyl]-2-pyrrolidinethione, respectively. Therefore, the previously proposed structure of these compounds of 2-piperidinethione skeleton should be revised.

Original language	English
Pages (from-to)	6757-6760
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	46
DOIs	https://doi.org/10.1016/S0040-4039(00)93595-0
Publication status	Published - 1991 Nov 11

Keywords

X-ray structure analysis
growth inhibitor
phototropism
radish hypocotyls
raphanusanins A and B

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)93595-0

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Revision of the structure of raphanusanins, phototropism-regulating substances of radish hypocotyls. / Harada, Nobuyuki; Hagiwara, Hisahiro; Ono, Hiroshi; Uda, Hisashi; Ohba, Shigeru; Kubota, Mari; Nishiyama, Shigeru; Yamamura, Shosuke; Hasegawa, Koji; Sakoda, Masako.

In: Tetrahedron Letters, Vol. 32, No. 46, 11.11.1991, p. 6757-6760.

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

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title = "Revision of the structure of raphanusanins, phototropism-regulating substances of radish hypocotyls",

abstract = "The structures of raphanusanins A and B, growth inhibitors involved in phototropism of radish hypocotyls, were determined by X-ray crystallographic structure analysis and by spectral studies to be (3R*,6R*)- and (3R*,6S*)-3-[methoxy(methylthio)methyl]-2-pyrrolidinethione, respectively. Therefore, the previously proposed structure of these compounds of 2-piperidinethione skeleton should be revised.",

keywords = "X-ray structure analysis, growth inhibitor, phototropism, radish hypocotyls, raphanusanins A and B",

author = "Nobuyuki Harada and Hisahiro Hagiwara and Hiroshi Ono and Hisashi Uda and Shigeru Ohba and Mari Kubota and Shigeru Nishiyama and Shosuke Yamamura and Koji Hasegawa and Masako Sakoda",

note = "Funding Information: Acknowledgment. This work was supportedi n part by grants from the Ministry of Education, Science, and Culture, Japan (General (A) No. 59430005a nd General (B) No. 01470026t o N.H., and priority Areas Nos. 02250103a nd 03236101t o N.H., S.Y., and K.H.).",

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AU - Harada, Nobuyuki

AU - Hagiwara, Hisahiro

AU - Ono, Hiroshi

AU - Uda, Hisashi

AU - Ohba, Shigeru

AU - Kubota, Mari

AU - Nishiyama, Shigeru

AU - Yamamura, Shosuke

AU - Hasegawa, Koji

AU - Sakoda, Masako

N1 - Funding Information: Acknowledgment. This work was supportedi n part by grants from the Ministry of Education, Science, and Culture, Japan (General (A) No. 59430005a nd General (B) No. 01470026t o N.H., and priority Areas Nos. 02250103a nd 03236101t o N.H., S.Y., and K.H.).

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AB - The structures of raphanusanins A and B, growth inhibitors involved in phototropism of radish hypocotyls, were determined by X-ray crystallographic structure analysis and by spectral studies to be (3R*,6R*)- and (3R*,6S*)-3-[methoxy(methylthio)methyl]-2-pyrrolidinethione, respectively. Therefore, the previously proposed structure of these compounds of 2-piperidinethione skeleton should be revised.

KW - X-ray structure analysis

KW - growth inhibitor

KW - phototropism

KW - radish hypocotyls

KW - raphanusanins A and B

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Revision of the structure of raphanusanins, phototropism-regulating substances of radish hypocotyls

Abstract

Keywords

ASJC Scopus subject areas

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