P450camr, a cytochrome P450 catalysing the stereospecific 6-endo-hydroxylation of (1R)-(+)-camphor

被引：22

作者：

Grogan, G ^{[1
]}

Roberts, GA ^{[1
]}

Parsons, S ^{[1
]}

Turner, NJ ^{[1
]}

Flitsch, SL ^{[1
]}

机构：

[1] Univ Edinburgh, Dept Chem, Edinburgh Ctr Prot technol, Edinburgh EH9 3JJ, Midlothian, Scotland

来源：

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY | 2002年 / 59卷 / 4-5期

基金：

英国生物技术与生命科学研究理事会;

关键词：

D O I：

10.1007/s00253-002-1054-0

中图分类号：

Q81 [生物工程学（生物技术）]; Q93 [微生物学];

学科分类号：

071005 ; 0836 ; 090102 ; 100705 ;

摘要：

Rhodococcus sp. NCIMB 9784 accumulated 6-endo-hydroxycamphor 3 when grown on (1R)-(+)camphor 1 as sole carbon source. The structure of 3 has been unambiguously assigned for the first time using Xray crystallography. A soluble cytochrome P450 hydroxylase, induced by growth on (1R)-(+)-camphor and designated P450(camr), has been isolated from the bacterium Rhodococcus sp. NCIMB 9784. Using authentic 6-endo hydroxycamphor as standard, a cell-free system consisting of pure P450(camr) and putidaredoxin and putidaredoxin reductase from Pseudomonas putida confirmed that the enzyme hydroxylates (1R)-(+)-camphor specifically in the 6-endo position, in contrast to the 5-exo hydroxylation catalysed by the well-studied P450(cam) from P. putida. P450(camr) has a molecular mass of approximately 44 kDa, and a pI of 4.8.

引用

页码：449 / 454

页数：6

共 18 条

[1] MICROBIOLOGICAL DEGRADATION OF (+)-CAMPHOR [J].

BRADSHAW, WH ;

CONRAD, HE ;

COREY, EJ ;

GUNSALUS, IC ;

LEDNICER, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (20) :5507-5507

[2] A NEW ACYCLIC ACID METABOLITE IN CAMPHOR OXIDATION [J].

CHAPMAN, PJ ;

MEERMAN, G ;

GUNSALUS, IC ;

SRINIVAS.R ;

RINEHART, KL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (03) :618-&

[3] AUTOCATALYTIC ALKYLATION OF THE CYTOCHROME-P-450 PROSTHETIC HEME GROUP BY 1-AMINOBENZOTRIAZOLE - ISOLATION OF AN NN-BRIDGED BENZENE-PROTOPORPHYRIN IX ADDUCT [J].

DEMONTELLANO, PRO ;

MATHEWS, JM .

BIOCHEMICAL JOURNAL, 1981, 195 (03) :761-764

[4] THE TOTAL SYNTHESIS OF (+)-RYANODOL .3. PREPARATION OF (+)-ANHYDRORYANODOL FROM A KEY PENTACYCLIC INTERMEDIATE [J].

DESLONGCHAMPS, P ;

BELANGER, A ;

BERNEY, DJF ;

BORSCHBERG, HJ ;

BROUSSEAU, R ;

DOUTHEAU, A ;

DURAND, R ;

KATAYAMA, H ;

LAPALME, R ;

LETURC, DM ;

LIAO, CC ;

MACLACHLAN, FN ;

MAFFRAND, JP ;

MARAZZA, F ;

MARTINO, R ;

MOREAU, C ;

RUEST, L ;

SAINTLAURENT, L ;

SAINTONGE, R ;

SOUCY, P .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (01) :153-185

[5] Biohydroxylation reactions catalyzed by enzymes and whole-cell systems [J].

Flitsch, SL ;

Aitken, SJ ;

Chow, CSY ;

Grogan, G ;

Staines, A .

BIOORGANIC CHEMISTRY, 1999, 27 (02) :81-90

[6] CYTOCHROME P-450(CAM) MONOOXYGENASE CAN BE REDESIGNED TO CATALYZE THE REGIOSELECTIVE AROMATIC HYDROXYLATION OF DIPHENYLMETHANE [J].

FOWLER, SM ;

ENGLAND, PA ;

WESTLAKE, ACG ;

ROUCH, DR ;

NICKERSON, DP ;

BLUNT, C ;

BRAYBROOK, D ;

WEST, S ;

WONG, LL ;

FLITSCH, SL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (24) :2761-2762

[7] CATABOLISM OF CAMPHOR IN TISSUE-CULTURES AND LEAF-DISKS OF COMMON SAGE (SALVIA-OFFICINALIS) [J].

FUNK, C ;

KOEPP, AE ;

CROTEAU, R .

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1992, 294 (01) :306-313

[8] BIOLOGICAL BAEYER-VILLIGER OXIDATION OF SOME MONOCYCLIC AND BICYCLIC KETONES USING MONOOXYGENASES FROM ACINETOBACTER-CALCOACETICUS NCIMB-9871 AND PSEUDOMONAS-PUTIDA NCIMB-10007 [J].

GAGNON, R ;

GROGAN, G ;

LEVITT, MS ;

ROBERTS, SM ;

WAN, PWH ;

WILLETTS, AJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (18) :2537-2543

[9]

Grogan G, 2001, ANGEW CHEM INT EDIT, V40, P1111, DOI 10.1002/1521-3773(20010316)40:6<1111::AID-ANIE11110>3.0.CO

[10]

2-2

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