An Arabidopsis oxidosqualene cyclase catalyzes iridal skeleton formation by Grob fragmentation

被引：62

作者：

Xiong, QB

Wilson, WK

Matsuda, SPT ^{[1
]}

机构：

[1] Rice Univ, Dept Chem, Houston, TX 77005 USA

[2] Rice Univ, Dept Biochem & Cell Biol, Houston, TX 77005 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 08期

关键词：

cyclization; fragmentation; iridals; oxidosqualene; terpenoids;

D O I：

10.1002/anie.200503420

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Mechanistic and phylogenetic surprises: A triterpene synthase (MRN1) from Arabidopsis invokes a Grob fragmentation in the cyclization of oxidosqualene. The enzymatic product is the elusive carbocyclic precursor of iridals, unusual triterpenoids known only in the distant Iris family. The results demonstrate the power of genome mining and exemplify the facile evolution of cyclases to generate diverse triterpene skeletons. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1285 / 1288

页数：4

共 55 条

[51] Structure and reactivity of the dammarenyl cation: Configurational transmission in triterpene synthesis
Xiong, QB
Rocco, F
Wilson, WK
Xu, R
Ceruti, M
Matsuda, SPT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) : 5362 - 5375
[52] Enzymatic synthesis of an indole diterpene by an oxidosqualene cyclase: Mechanistic, biosynthetic, and phylogenetic implications
Xiong, QB
Zhu, XW
Wilson, WK
Ganesan, A
Matsuda, SPT
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (30) : 9002 - 9003
[53] On the origins of triterpenoid skeletal diversity
Xu, R
Fazio, GC
Matsuda, SPT
[J]. PHYTOCHEMISTRY, 2004, 65 (03) : 261 - 291
[54] Yoshida T., 2000, CURRENT TOPICS PHYTO, V4, P135
[55] GENEVESTIGATOR. Arabidopsis microarray database and analysis toolbox
Zimmermann, P
Hirsch-Hoffmann, M
Hennig, L
Gruissem, W
[J]. PLANT PHYSIOLOGY, 2004, 136 (01) : 2621 - 2632

← 1 2 3 4 5 6 →