Stabilisation of eudesmane cation by tryptophan 334 during aristolochene synthase catalysis

被引：37

作者：

Deligeorgopoulou, A ^{[1
]}

Taylor, SE ^{[1
]}

Forcat, S ^{[1
]}

Allemann, RK ^{[1
]}

机构：

[1] Univ Birmingham, Sch Chem Sci, Birmingham B15 2TT, W Midlands, England

来源：

CHEMICAL COMMUNICATIONS | 2003年 / 17期

关键词：

D O I：

10.1039/b306867f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Analysis of the hydrocarbons produced during catalysis by mutants of aristolochene synthase from Penicillium roqueforti indicated that Trp 334 had a pivotal function for the efficient production of aristolochene from farnesylpyrophosphate most likely by stabilising the intermediate, eudesmane cation.

引用

页码：2162 / 2163

页数：2

共 18 条

[1] Tyrosine 92 of aristolochene synthase directs cyclisation of farnesyl pyrophosphate [J].

Calvert, MJ ;

Taylor, SE ;

Allemann, RK .

CHEMICAL COMMUNICATIONS, 2002, (20) :2384-2385

[2] Germacrene A is a product of the aristolochene synthase-mediated conversion of farnesylpyrophosphate to aristolochene [J].

Calvert, MJ ;

Ashton, PR ;

Allemann, RK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11636-11641

[3] ENZYMATIC FORMATION OF SESQUITERPENES [J].

CANE, DE .

CHEMICAL REVIEWS, 1990, 90 (07) :1089-1103

[4] Aristolochene synthase. Elucidation of the cryptic germacrene A synthase activity using the anomalous substrate dihydrofarnesyl diphosphate [J].

Cane, DE ;

Tsantrizos, YS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (42) :10037-10040

[5] ARISTOLOCHENE SYNTHASE - MECHANISM-BASED INHIBITION OF A TERPENOID CYCLASE [J].

CANE, DE ;

BRYANT, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :12063-12064

[6] ARISTOLOCHENE BIOSYNTHESIS AND ENZYMATIC CYCLIZATION OF FARNESYL PYROPHOSPHATE [J].

CANE, DE ;

PRABHAKARAN, PC ;

SALASKI, EJ ;

HARRISON, PHM ;

NOGUCHI, H ;

RAWLINGS, BJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) :8914-8916

[7] Crystal structure determination of aristolochene synthase from the blue cheese mold, Penicillium roqueforti [J].

Caruthers, JM ;

Kang, I ;

Rynkiewicz, MJ ;

Cane, DE ;

Christianson, DW .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2000, 275 (33) :25533-25539

[8] Evidence for differential folding of farnesyl pyrophosphate in the active site of aristolochene synthase:: A single-point mutation converts aristolochene synthase into an (E)-β-farnesene synthase [J].

Deligeorgopoulou, A ;

Allemann, RK .

BIOCHEMISTRY, 2003, 42 (25) :7741-7747

[9]

Glasby J. S., 1982, ENCY TERPENOIDS

[10] Molecular scaffolds for chemical wizardry: Learning nature's rules for terpene cyclases [J].

Greenhagen, B ;

Chappell, J .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2001, 98 (24) :13479-13481

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