Brz220 a novel brassinosteroid biosynthesis inhibitor: stereochemical structure-activity relationship

被引：17

作者：

Sekimata, K

Uzawa, J

Han, SY

Yoneyama, K

Takeuchi, Y

Yoshida, S

Asami, T

机构：

[1] RIKEN, Wako, Saitama 3510198, Japan

[2] Saitama Univ, Grad Sch Sci & Engn, Urawa, Saitama 3388570, Japan

[3] Utsunomiya Univ, Ctr Res Wild Plants, Utsunomiya, Tochigi 3218505, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 17期

关键词：

D O I：

10.1016/S0957-4166(02)00475-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The four stereoisomers of Brz220 (2RS,4RS-1-[4-propyl-2-(4-trifluoromethylphenyl)-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole), a novel brassinosteroid biosynthesis inhibitor. were separated by silica gel column chromatography and chiral high-performance liquid chromatography (HPLC). The absolute configuration of each stereoisomer was determined by a combination of asymmetric synthesis and NMR analysis. The effects of these stereoisomers on cress stem elongation clearly indicate that the (2S)-isomer has the greatest inhibitory activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：1875 / 1878

页数：4

相关论文

共 15 条

[1]

AREN EJ, 1988, J BIOLOCHEM PHARM, V37, P9

[2] Brassinosteroid biosynthesis inhibitors [J].

Asami, T ;

Yoshida, S .

TRENDS IN PLANT SCIENCE, 1999, 4 (09) :348-353

[3] Selective interaction of triazole derivatives with DWF4, a cytochrome P450 monooxygenase of the brassinosteroid biosynthetic pathway, correlates with brassinosteroid deficiency in Planta [J].

Asami, T ;

Mizutani, M ;

Fujioka, S ;

Goda, H ;

Min, YK ;

Shimada, Y ;

Nakano, T ;

Takatsuto, S ;

Matsuyama, T ;

Nagata, N ;

Sakata, K ;

Yoshida, S .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (28) :25687-25691

[4] Characterization of brassinazole, a triazole-type brassinosteroid biosynthesis inhibitor [J].

Asami, T ;

Min, YK ;

Nagata, N ;

Yamagishi, K ;

Takatsuto, S ;

Fujioka, S ;

Murofushi, N ;

Yamaguchi, I ;

Yoshida, S .

PLANT PHYSIOLOGY, 2000, 123 (01) :93-99

[5] Plants steroid hormones, brassinosteroids: Current highlights of molecular aspects on their synthesis/metabolism, transport, perception and response [J].

Bishop, GJ ;

Yokota, T .

PLANT AND CELL PHYSIOLOGY, 2001, 42 (02) :114-120

[6] SOLID-STATE STRUCTURE DETERMINATION AND SOLUTION-STATE NMR CHARACTERIZATION OF THE (2R,4R)/(2S,4S)-DIASTEREOMERS AND (2R,4S)/(2S,4R)-DIASTEREOMERS OF THE AGRICULTURAL FUNGICIDE PROPICONAZOLE, THE (2R,4S)/(2S,4R)-SYMMETRICAL TRIAZOLE CONSTITUTIONAL ISOMER, AND A DITRIAZOLE ANALOG [J].

GLASER, R ;

ADIN, I ;

OVADIA, D ;

MENDLER, E ;

DROUIN, M .

STRUCTURAL CHEMISTRY, 1995, 6 (03) :145-156

[7] New lead compounds for brassinosteroid biosynthesis inhibitors [J].

Min, YK ;

Asami, T ;

Fujioka, S ;

Murofushi, N ;

Yamaguchi, I ;

Yoshida, S .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (03) :425-430

[8] Treatment of dark-grown Arabidopsis thaliana with a brassinosteroid-biosynthesis inhibitor, brassinazole, induces some characteristics of light-grown plants [J].

Nagata, N ;

Min, YK ;

Nakano, T ;

Asami, T ;

Yoshida, S .

PLANTA, 2000, 211 (06) :781-790

[9] Brassinazole, an inhibitor of brassinosteroid biosynthesis, inhibits development of secondary xylem in cress plants (Lepidium sativum) [J].

Nagata, N ;

Asami, T ;

Yoshida, S .

PLANT AND CELL PHYSIOLOGY, 2001, 42 (09) :1006-1011

[10]

SASSE J, 1999, PHYSL ACTIONS BRASSI, P137