Structure of limonene synthase, a simple model for terpenoid cyclase catalysis

被引:179
作者
Hyatt, David C.
Youn, Buhyun
Zhao, Yuxin
Santhamma, Bindu
Coates, Robert M.
Croteau, Rodney B. [1 ]
Kang, Chulhee
机构
[1] Washington State Univ, Inst Biol Chem, Pullman, WA 99164 USA
[2] Washington State Univ, Sch Mol Biosci, Pullman, WA 99164 USA
[3] Univ Illinois, Dept Chem, Urbana, IL 61801 USA
关键词
crystal structure; geranyl diphosphate; linalyl diphosphate; monoterpene cyclase; monoterpene synthase;
D O I
10.1073/pnas.0700915104
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
The crystal structure of (4S)-limonene synthase from Meniha spicata, a metal ion-dependent monoterpene cyclase that catalyzes the coupled isomerization and cyclization of geranyl diphosphate, is reported at 2.7-angstrom resolution in two forms liganded to the substrate and intermediate analogs, 2-fluorogeranyl diphosphate and 2-fluorolinalyl diphosphate, respectively. The implications of these findings are described for domain interactions in the homodimer and for changes in diphosphate-metal ion coordination and substrate binding conformation in the course of the multistep reaction.
引用
收藏
页码:5360 / 5365
页数:6
相关论文
共 61 条
[41]   Bifunctional abietadiene synthase: Free diffusive transfer of the (+)-copalyl diphosphate intermediate between two distinct active sites [J].
Peters, RJ ;
Ravn, MM ;
Coates, RM ;
Croteau, RB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :8974-8978
[42]   Abietadiene synthase from grand fir (Abies grandis):: Characterization and mechanism of action of the "pseudomature" recombinant enzyme [J].
Peters, RJ ;
Flory, JE ;
Jetter, R ;
Ravn, MM ;
Lee, HJ ;
Coates, RM ;
Croteau, RB .
BIOCHEMISTRY, 2000, 39 (50) :15592-15602
[43]   MODEL STUDIES OF TERPENE BIOSYNTHESIS - A STEPWISE MECHANISM FOR CYCLIZATION OF NEROL TO ALPHA-TERPINEOL [J].
POULTER, CD ;
KING, CHR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (05) :1422-1424
[44]   FARNESYLPYROPHOSPHATE SYNTHETASE - A STEPWISE MECHANISM FOR THE 1'-4 CONDENSATION REACTION [J].
POULTER, CD ;
WIGGINS, PL ;
LE, AT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (13) :3926-3927
[45]   MECHANISM OF PRENYL-TRANSFER REACTION - STUDIES WITH (E)-3-TRIFLUOROMETHYL-2-BUTEN-1-YL AND (Z)-3-TRIFLUOROMETHYL-2-BUTEN-1-YL PYROPHOSPHATE [J].
POULTER, CD ;
SATTERWHITE, DM .
BIOCHEMISTRY, 1977, 16 (25) :5470-5478
[46]  
POULTER CD, 1978, J BIOL CHEM, V253, P7227
[47]   REGIOSPECIFICITY AND ISOTOPE EFFECTS ASSOCIATED WITH THE METHYL METHYLENE ELIMINATIONS IN THE ENZYME-CATALYZED BIOSYNTHESIS OF (R)-LIMONENE AND (S)-LIMONENE [J].
PYUN, HJ ;
COATES, RM ;
WAGSCHAL, KC ;
MCGEADY, P ;
CROTEAU, RB .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3998-4009
[48]   CHARACTERIZATION AND MECHANISM OF (4S)-LIMONENE SYNTHASE, A MONOTERPENE CYCLASE FROM THE GLANDULAR TRICHOMES OF PEPPERMINT (MENTHA X PIPERITA) [J].
RAJAONARIVONY, JIM ;
GERSHENZON, J ;
CROTEAU, R .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1992, 296 (01) :49-57
[49]   EVIDENCE FOR AN ESSENTIAL HISTIDINE RESIDUE IN 4S-LIMONENE SYNTHASE AND OTHER TERPENE CYCLASES [J].
RAJAONARIVONY, JIM ;
GERSHENZON, J ;
MIYAZAKI, J ;
CROTEAU, R .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1992, 299 (01) :77-82
[50]  
SATTERWHITE DM, 1985, J BIOL CHEM, V260, P3901