Fluorinated fatty acids: New mechanistic probes for desaturases

被引:13
作者
Buist, PH [1 ]
Behrouzian, B [1 ]
Alexopoulos, KA [1 ]
Dawson, B [1 ]
Black, B [1 ]
机构
[1] HLTH CANADA,HLTH PROTECT BRANCH,DRUGS DIRECTORATE,BUR DRUG RES,OTTAWA,ON K1A 0L2,CANADA
关键词
D O I
10.1039/cc9960002671
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Only (E)-fluoroalkenic products are obtained when racemic 9- and 10-fluoro fatty acids are processed by a Saccharomyces cerevisiae Delta 9 desaturase as determined by H-1-decoupled F-19 NMR and GC-MS analysis; no evidence for hydroxylated intermediates was found.
引用
收藏
页码:2671 / 2672
页数:2
相关论文
共 14 条
[1]   Use of F-19 NMR as a direct probe of Delta(9) desaturase cryptoregiochemistry: A feasibility study [J].
Buist, P ;
Marecak, D ;
Dawson, B ;
Black, B .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1996, 74 (03) :453-456
[2]   Use of deuterium kinetic isotope effects to probe the cryptoregiochemistry of Delta 9 desaturation [J].
Buist, PH ;
Behrouzian, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (26) :6295-6296
[3]   STEREOCHEMICAL ANALYSIS OF SULFOXIDES OBTAINED BY DIVERTED DESATURATION [J].
BUIST, PH ;
MARECAK, DM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5073-5080
[4]  
BUIST PH, UNPUB
[5]   Regiochemical variations in reactions of methylcubane with tert-butoxyl radical, cytochrome P-450 enzymes, and a methane monooxygenase system [J].
Choi, SY ;
Eaton, PE ;
Hollenberg, PF ;
Liu, KE ;
Lippard, SJ ;
Newcomb, M ;
Putt, DA ;
Upadhyaya, SP ;
Xiong, YS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (28) :6547-6555
[6]   RESONANCE RAMAN EVIDENCE FOR AN FE-O-FE CENTER IN STEAROYL-ACP DESATURASE - PRIMARY SEQUENCE IDENTITY WITH OTHER DIIRON-OXO PROTEINS [J].
FOX, BG ;
SHANKLIN, J ;
AI, JY ;
LOEHR, TM ;
SANDERSLOEHR, J .
BIOCHEMISTRY, 1994, 33 (43) :12776-12786
[7]   MICROBIAL HYDROXYLATION OF STEROIDS .8. INCUBATION OF CN HALOXYLATING AND OTHER SUBSTITUTED STEROIDS WITH CN HYDROXYLATING FUNGI [J].
HOLLAND, HL ;
THOMAS, EM .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (02) :160-164
[8]   STEREOSPECIFIC SYNTHESIS OF ALKENYL FLUORIDES (WITH RETENTION) VIA ORGANOMETALLIC INTERMEDIATES [J].
LEE, SH ;
SCHWARTZ, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (09) :2445-2447
[9]   REGIOCHEMICAL DISTRIBUTION OF DEUTERIUM DURING FATTY-ACID BIOSYNTHESIS FOLLOWING INCORPORATION OF [2-C-13, 2-H-2(3)] ACETATE - A C-13 NMR-STUDY OF EXCHANGE, DESATURASE AND ENOYL REDUCTASE STEREOSPECIFICITIES IN 3 ALGAE AND A YEAST [J].
MCINNES, AG ;
WALTER, JA ;
WRIGHT, JLC .
TETRAHEDRON, 1983, 39 (21) :3515-3522
[10]   REGIOSELECTIVE OPENING OF SIMPLE EPOXIDES WITH DIISOPROPYLAMINE TRIHYDROFLUORIDE [J].
MUEHLBACHER, M ;
POULTER, CD .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1026-1030