Trichodiene synthase: Mechanism-based inhibition of a sesquiterpene cyclase

被引：13

作者：

Cane, DE ^{[1
]}

Bowser, TE ^{[1
]}

机构：

[1] Brown Univ, Dept Chem, Providence, RI 02912 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1999年 / 9卷 / 08期

关键词：

D O I：

10.1016/S0960-894X(99)00149-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The 10-cyclopropylidene analog of farnesyl diphosphate was shown to be a mechanism-based inhibitor of trichodiene synthase with an inactivation rate (k(inact)) of 0.010 +/- 0.0003 min(-1) and an apparent K-I of 663 +/- 75 nM. The presence of three anomalous sesquiterpene products detected in incubation mixtures indicate that the compound also serves as a substrate of the enzyme. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：1127 / 1132

页数：6

相关论文

共 32 条

[1] ENZYMATIC FORMATION OF SESQUITERPENES [J].

CANE, DE .

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

[2] TRICHODIENE SYNTHASE - STEREOCHEMICAL STUDIES OF THE CRYPTIC ALLYLIC DIPHOSPHATE ISOMERASE ACTIVITY USING AN ANOMALOUS SUBSTRATE [J].

CANE, DE ;

YANG, GH .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5794-5798

[3] TRICHODIENE BIOSYNTHESIS AND THE ENZYMATIC CYCLIZATION OF FARNESYL PYROPHOSPHATE [J].

CANE, DE ;

SWANSON, S ;

MURTHY, PPN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2136-2138

[4] ISOPRENOID BIOSYNTHESIS - STEREOCHEMISTRY OF THE CYCLIZATION OF ALLYLIC PYROPHOSPHATES [J].

CANE, DE .

ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (07) :220-226

[5] TRICHODIENE BIOSYNTHESIS AND THE ROLE OF NEROLIDYL PYROPHOSPHATE IN THE ENZYMATIC CYCLIZATION OF FARNESYL PYROPHOSPHATE [J].

CANE, DE ;

HA, HJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6865-6870

[6] TRICHODIENE SYNTHASE - SYNERGISTIC INHIBITION BY INORGANIC PYROPHOSPHATE AND AZA ANALOGS OF THE BISABOLYL CATION [J].

CANE, DE ;

YANG, GH ;

COATES, RM ;

PYUN, HJ ;

HOHN, TM .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3454-3462

[7] TRICHODIENE SYNTHASE - SUBSTRATE-SPECIFICITY AND INHIBITION [J].

CANE, DE ;

YANG, GH ;

XUE, Q ;

SHIM, JH .

BIOCHEMISTRY, 1995, 34 (08) :2471-2479

[8] OVERPRODUCTION OF SOLUBLE TRICHODIENE SYNTHASE FROM FUSARIUM-SPOROTRICHIOIDES IN ESCHERICHIA-COLI [J].

CANE, DE ;

ZHEN, W ;

OLIVER, JS ;

HOHN, TM .

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1993, 300 (01) :416-422

[9] CYCLONERODIOL BIOSYNTHESIS AND THE ENZYMATIC CONVERSION OF FARNESYL TO NEROLIDYL PYROPHOSPHATE [J].

CANE, DE ;

IYENGAR, R ;

SHIAO, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (04) :914-931

[10] TRICHODIENE BIOSYNTHESIS AND THE STEREOCHEMISTRY OF THE ENZYMATIC CYCLIZATION OF FARNESYL PYROPHOSPHATE [J].

CANE, DE ;

HA, HJ ;

PARGELLIS, C ;

WALDMEIER, F ;

SWANSON, S ;

MURTHY, PPN .

BIOORGANIC CHEMISTRY, 1985, 13 (03) :246-265

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