The fluorinase from Streptomyces cattleya is also a chlorinase

被引:80
作者
Deng, H
Cobb, SL
McEwan, AR
McGlinchey, RP
Naismith, JH
O'Hagan, D [1 ]
Robinson, DA
Spencer, JB
机构
[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland
[2] Univ St Andrews, Ctr Biomol Sci, St Andrews KY16 9ST, Fife, Scotland
[3] Univ Cambridge, Chem Labs, Cambridge CB2 1EW, England
基金
英国生物技术与生命科学研究理事会;
关键词
chlorinase; enzyme catalysis; fluorinase; halogenation; S-adenosylmethionine;
D O I
10.1002/anie.200503582
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Choices choices: The fluorinase enzyme from Streptomyces cattleya (catalyzes the formation of a C-F bond from fluoride ions) also has the capacity to utilize a chloride ion although it has a clear preference for the fluoride ion. The enzyme mediates a nucleophilic chlorination reaction, which is an unusual mechanism for enzymatic chlorination. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:759 / 762
页数:4
相关论文
共 24 条
[1]   The role of vanadium bromoperoxidase in the biosynthesis of halogenated marine natural products [J].
Butler, A ;
Carter-Franklin, JN .
NATURAL PRODUCT REPORTS, 2004, 21 (01) :180-188
[2]   Enzymatic fluorination in Streptomyces cattleya takes place with an inversion of configuration consistent with an SN2 reaction mechanism [J].
Cadicamo, CD ;
Courtieu, J ;
Deng, H ;
Meddour, A ;
O'Hagan, D .
CHEMBIOCHEM, 2004, 5 (05) :685-690
[3]   Identification of 5-fluoro-5-deoxy-D-ribose-1-phosphate as an intermediate in fluorometabolite biosynthesis in Streptomyces cattleya [J].
Cobb, SL ;
Deng, H ;
Hamilton, JTG ;
McGlinchey, RP ;
O'Hagan, D .
CHEMICAL COMMUNICATIONS, 2004, (05) :592-593
[4]  
COBB SL, 2005, THESIS U ST ANDREWS
[5]   Fluorometabolite biosynthesis and the fluorinase from Streptomyces cattleya [J].
Deng, H ;
O'Hagan, D ;
Schaffrath, C .
NATURAL PRODUCT REPORTS, 2004, 21 (06) :773-784
[6]   Tryptophan 7-halogenase (PrnA) structure suggests a mechanism for regioselective chlorination [J].
Dong, CJ ;
Flecks, S ;
Unversucht, S ;
Haupt, C ;
van Pée, KH ;
Naismith, JH .
SCIENCE, 2005, 309 (5744) :2216-2219
[7]   Crystal structure and mechanism of a bacterial fluorinating enzyme [J].
Dong, CJ ;
Huang, FL ;
Deng, H ;
Schaffrath, C ;
Spencer, JB ;
O'Hagan, D ;
Naismith, JH .
NATURE, 2004, 427 (6974) :561-565
[8]   THE FLUORINATED NATURAL-PRODUCTS [J].
HARPER, DB ;
OHAGAN, D .
NATURAL PRODUCT REPORTS, 1994, 11 (02) :123-133
[9]   AMP-DEAMINASE AS A NOVEL PRACTICAL CATALYST IN THE SYNTHESIS OF 6-OXOPURINE RIBOSIDES AND THEIR ANALOGS [J].
MARGOLIN, AL ;
BORCHERDING, DR ;
WOLFKUGEL, D ;
MARGOLIN, N .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (24) :7214-7218
[10]  
Murphy CD, 2001, ANGEW CHEM INT EDIT, V40, P4479, DOI 10.1002/1521-3773(20011203)40:23<4479::AID-ANIE4479>3.0.CO