A putative precursor of isomalabaricane triterpenoids from lanosterol synthase mutants

被引：35

作者：

Lodeiro, S

Wilson, WK

Shan, H

Matsuda, SPT

机构：

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

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

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 03期

关键词：

D O I：

10.1021/ol052725j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Known lanosterol synthase mutants produce monocyclic or tetracyclic byproducts from oxidosqualene. We describe Erg7 Tyr510 mutants that cause partial substrate misfolding and generate a tricyclic byproduct. This novel triterpene, (13 alpha H)-isomalabarica-14(27),17E,21-trien-3 beta-ol, is the likely biosynthetic precursor of isomalabaricane triterpenoids in sponges. The results suggest the facile evolution of protective triterpenoids in sessile animals.

引用

收藏

页码：439 / 442

页数：4

相关论文

共 39 条

[31] Insight into steroid scaffold formation from the structure of human oxidosqualene cyclase [J].

Thoma, R ;

Schulz-Gasch, T ;

D'Arcy, B ;

Benz, J ;

Aebi, J ;

Dehmlow, H ;

Hennig, M ;

Stihle, M ;

Ruf, A .

NATURE, 2004, 432 (7013) :118-122

[32] NONENZYMIC LABORATORY CYCLIZATION OF SQUALENE 2,3-OXIDE [J].

VAN TAMELEN, EE ;

WILLET, J ;

SCHWARTZ, M ;

NADEAU, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (24) :5937-+

[33] ENZYMIC CYCLIZATION OF TRANS TRANS TRANS-18,19-DIHYDROSQUALENE 2,3-OXIDE [J].

VAN TAMELEN, EE ;

SHARPLESS, KB ;

HANZLIK, R ;

CLAYTON, RB ;

BURLINGAME, AL ;

WSZOLEK, PC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (26) :7150-+

[34]

Wendt KU, 2000, ANGEW CHEM INT EDIT, V39, P2812, DOI 10.1002/1521-3773(20000818)39:16<2812::AID-ANIE2812>3.0.CO

[35]

2-#

[36] Histidine residue at position 234 of oxidosqualene-lanosterol cyclase from Saccharomyces cerevisiae simultaneously influences cyclization, rearrangement, and deprotonation reactions [J].

Wu, TK ;

Liu, YT ;

Chang, CH .

CHEMBIOCHEM, 2005, 6 (07) :1177-+

[37] Enzymatic formation of multiple triterpenes by mutation of tyrosine 510 of the oxidosqualene-lanosterol cyclase from Saccharomyces cerevisiae [J].

Wu, TK ;

Chang, CH .

CHEMBIOCHEM, 2004, 5 (12) :1712-1715

[38] Structure and reactivity of the dammarenyl cation: Configurational transmission in triterpene synthesis [J].

Xiong, QB ;

Rocco, F ;

Wilson, WK ;

Xu, R ;

Ceruti, M ;

Matsuda, SPT .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) :5362-5375

[39] On the origins of triterpenoid skeletal diversity [J].

Xu, R ;

Fazio, GC ;

Matsuda, SPT .

PHYTOCHEMISTRY, 2004, 65 (03) :261-291

← 1 2 3 4 →