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

School of Medicine

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

14 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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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.).",

year = "1991",

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doi = "10.1016/S0040-4039(00)93595-0",

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volume = "32",

pages = "6757--6760",

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T1 - Revision of the structure of raphanusanins, phototropism-regulating substances of radish hypocotyls

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.).

PY - 1991/11/11

Y1 - 1991/11/11

N2 - 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.

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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U2 - 10.1016/S0040-4039(00)93595-0

DO - 10.1016/S0040-4039(00)93595-0

M3 - Article

AN - SCOPUS:0026094366

VL - 32

SP - 6757

EP - 6760

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 46

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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