MICROBIAL TRANSFORMATIONS .18. REGIOSPECIFIC PARA-HYDROXYLATION OF AROMATIC CARBAMATES MEDIATED BY THE FUNGUS BEAUVERIA-SULFURESCENS

被引:31
作者
VIGNE, B [1 ]
ARCHELAS, A [1 ]
FURSTOSS, R [1 ]
机构
[1] FAC SCI LUMINY,CHIM ORGAN & BIOORGAN LAB,70 ROUTE LEON LACHAMP,CASE 901,F-13288 MARSEILLE 9,FRANCE
关键词
D O I
10.1016/S0040-4020(01)86421-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The bioconversion of various N-phenyl carbamates bearing alkyl groups of increasing size have been studied. These biotransformations, achieved by the fungus Beauveria sulfurescens, led to the highly regiospecific para-hydroxylation of most of the substrates. For compounds of higher lipophilic character, a double regio- and stereospecific hydroxylation process occurred, which included aromatic and alkyl hydroxylation.
引用
收藏
页码:1447 / 1458
页数:12
相关论文
共 17 条
[1]   MICROBIAL TRANSFORMATIONS .8. 1ST EXAMPLE OF A HIGHLY ENANTIOSELECTIVE MICROBIOLOGICAL HYDROXYLATION PROCESS [J].
ARCHELAS, A ;
FOURNERON, JD ;
FURSTOSS, R ;
CESARIO, M ;
PASCARD, C .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1797-1799
[2]   SYNTHESIS OF 2,5,6-TRIDEOXYSTREPTAMINE AND ITS TRANSFORMATION INTO BIOACTIVE PSEUDO-DISACCHARIDES BY MICROBIAL AND CHEMICAL METHODS [J].
COLAS, C ;
QUICLETSIRE, B ;
CLEOPHAX, J ;
DELAUMENY, JM ;
SEPULCHRE, AM ;
GERO, SD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (02) :857-858
[3]   C-13 NUCLEAR MAGNETIC-RESONANCE SPECTRA .1. MONOSUBSTITUTED ADAMANTANES AND ADAMANTANONES [J].
DUDDECK, H .
ORGANIC MAGNETIC RESONANCE, 1975, 7 (04) :151-153
[4]  
ELSHARKAWY S, 1986, J NAT PRODUCTS, V50, P520
[5]   MICROBIAL TRANSFORMATIONS .7. BIOHYDROXYLATION OF BORNYLAMIDE DERIVATIVES BY THE FUNGUS BEAUVERIA SULFURESCENS [J].
FOURNERON, JD ;
ARCHELAS, A ;
VIGNE, B ;
FURSTOSS, R .
TETRAHEDRON, 1987, 43 (10) :2273-2284
[6]  
FURSTOSS R, 1986, NATO ASI SER, V178, P361
[7]  
JACQUESY JC, 1986, B SOC CHIM FR, V25, P625
[8]  
KOMIYAM AM, 1989, J CHEM SOC P1, P2031
[9]  
MARCH J, 1985, ADV ORG CHEM, P498
[10]   OXYFUNCTIONALIZATION OF HYDROCARBONS .14. ELECTROPHILIC HYDROXYLATION OF AROMATICS WITH BIS(TRIMETHYLSILYL) PEROXIDE TRIFLIC ACID [J].
OLAH, GA ;
ERNST, TD .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (05) :1204-1206