Importance of Saccharomyces cerevisiae Oxidosqualene-Lanosterol Cyclase Tyrosine 707 Residue for Chair-Boat Bicyclic Ring Formation and Deprotonation Reactions

被引：24

作者：

Wu, Tung-Kung ^{[1
]}

Wang, Tsai-Ting ^{[1
]}

Chang, Cheng-Hsiang ^{[1
]}

Liu, Yuan-Ting ^{[1
]}

Shie, Wen-Shiang ^{[1
]}

机构：

[1] Natl Chiao Tung Univ, Dept Biol Sci & Technol, Hsinchu 300, Taiwan

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 21期

关键词：

D O I：

10.1021/ol802036c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A contact mapping strategy was applied to identity putative amino acid residues that influence the oxidosqualene-lanosterol B-ring cyclization reaction. A bicyclic intermediate with two altered deprotonation products, in conjunction with lanosterol, were isolated from the ERG7(Y707X) mutants, indicating that the Tyr707 residue may play a functional role in stabilizing the chair-boat bicyclic C-8 cation and the lanosteryl C-8/C-9 cation intermediates.

引用

页码：4959 / 4962

页数：4

共 12 条

[1] Histidine residue at position 234 of oxidosqualene-lanosterol cyclase from Saccharomyces cerevisiae simultaneously influences cyclization, rearrangement, and deprotonation reactions
Wu, TK
Liu, YT
Chang, CH
CHEMBIOCHEM, 2005, 6 (07) : 1177 - +
[2] Phenylalanine 445 within oxidosqualene-lanosterol cyclase from Saccharomyces cerevisiae influences C-ring cyclization and deprotonation reactions
Wu, Tung-Kung
Liu, Yuan-Ting
Chiu, Feng-Hsuan
Chang, Cheng-Hsiang
ORGANIC LETTERS, 2006, 8 (21) : 4691 - 4694
[3] Tryptophan 232 within oxidosqualene-lanosterol cyclase from Saccharomyces cerevisiae influences rearrangement and deprotonation but not cyclization reactions
Wu, TK
Yu, MT
Liu, YT
Chang, CH
Wang, HJ
Diau, EWG
ORGANIC LETTERS, 2006, 8 (07) : 1319 - 1322
[4] Enzymatic formation of multiple triterpenes by mutation of tyrosine 510 of the oxidosqualene-lanosterol cyclase from Saccharomyces cerevisiae
Wu, TK
Chang, CH
CHEMBIOCHEM, 2004, 5 (12) : 1712 - 1715
[5] Enzymatic formation of multiple triterpenes by mutation of tyrosine 510 of the oxidosqualene-lanosterol cyclase from Saccharomyces cerevisiae.
Chang, CH
Wu, TK
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U567 - U567
[6] Differential Stereocontrolled Formation of Tricyclic Triterpenes by Mutation of Tyrosine 99 of the Oxidosqualene-Lanosterol Cyclase from Saccharomyces cerevisiae
Wu, Tung-Kung
Li, Wen-Hsuan
Chang, Cheng-Hsiang
Wen, Hao-Yu
Liu, Yuan-Ting
Chang, Yi-Chun
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (33) : 5731 - 5737
[7] Altering oxidosqualene cyclization from chair-boat-chair to chair-chair-chair biosynthetic route by a single amino acid substitution at the phenylalanine 699 position of the Saccharomyces cerevisiae oxidosqualene-lanosterol cyclase
Wu, Tung-Kung
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238 : 761 - 761
[8] ORGN 610-Identification of a putative active site residue within oxidosqualene-lanosterol cyclase from saccharomyces cerevisiae that influences B/C ring cyclization
Li, Wen-Hsuan
Wu, Tung-Kung
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
[9] ORGN 608-Enzymatic formation of multiple triterpenes by mutation of histidine 234 of the oxidosqualene-lanosterol cyclase from saccharomyces cerevisiae
Liu, Yuan-Ting
Wu, Tung-Kung
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
[10] Site-saturated mutagenesis of histidine 234 of Saccharomyces cerevisiae oxidosqualene-lanosterol cyclase demonstrates dual functions in cyclization and rearrangement reactions
Wu, Tung-Kung
Liu, Yuan-Ting
Chang, Cheng-Hsiang
Yu, Mei-Ting
Wang, Hisng-Ju
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (19) : 6414 - 6419

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