Different reaction mechanisms for cis- and trans-prenyltransferases

被引：27

作者：

Lu, Yen-Pin ^{[2
]}

Liu, Hun-Ge ^{[1
]}

Liang, Po-Huang ^{[1
,2
]}

机构：

[1] Acad Sinica, Inst Biol Chem, Taipei 115, Taiwan

[2] Natl Taiwan Univ, Inst Biochem Sci, Taipei 106, Taiwan

来源：

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS | 2009年 / 379卷 / 02期

关键词：

Isoprenoid; Prenyltransferase; Reaction mechanism; Sequential; Concerted; UNDECAPRENYL-PYROPHOSPHATE SYNTHASE; PRODUCT CHAIN-LENGTH; PRENYL-TRANSFER-REACTION; STATE KINETIC-ANALYSIS; DIPHOSPHATE SYNTHASE; ESCHERICHIA-COLI; CRYSTAL-STRUCTURE; ISOPRENOID BIOSYNTHESIS; PURIFICATION; SYNTHETASE;

D O I：

10.1016/j.bbrc.2008.12.061

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Octaprenyl diphosphate synthase (OPPs) and undecaprenyl diphosphate synthases (UPPs) catalyze consecutive condensation reactions of farnesyl diphosphate (FPP) with 5 and 8 isopentenyl diphosphate (IPP) to generate C-40 and C-55 products With trans- and cis-double bonds, respectively. In this Study, we used IPP analogue, 3-bromo-3-butenyl diphosphate (Br-IPP), in conjunction with radiolabeled FPP, to probe the reaction mechanisms of the two prenyltransferases. Using this alternative substrate with electron-withdrawing bromo group at the G position to slow down the condensation step, trapping of farnesol in the OPPs reaction from radiolabeled FPP Under basic condition was observed, consistent with a sequential mechanism. In contrast, UPPs reaction yielded no farnesyl carbocation intermediate under the same condition with radiolabeled FPP and Br-IPP, indicating a concerted mechanism. Our data demonstrate the different reaction mechanisms for cis- and tran-prenyltransferases although they share the same substrates. (c) 2008 Elsevier Inc. All rights reserved

引用

页码：351 / 355

页数：5

共 27 条

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