Enzymatic resolution of 2,2,2-trifluoro-1-(1-pyrenyl)ethanol with lipases

被引:8
作者
Kato, K
Katayama, M
Fujii, S
Kimoto, H
机构
[1] Department of Chemistry, National Industrial Research Institute of Nagoya, Nagoya, Hirate-cho, Kita-ku
关键词
lipase; enantioselective alcoholysis; enzymatic resolution; CATALYZED OPTICAL RESOLUTION; ACYLATION;
D O I
10.1271/bbb.61.194
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
The optical resolution of (+/-)-2,2,2-trifluoro-1-(1-pyrenyl)ethanol was achieved by using lipases. In particular, Pseudomonas aeruginosa lipase (lipase LIP) showed high enantioselectivity (E = > 100) and reactivity in the alcoholysis of the chloroacetyl ester of the title compound, The reactivity of the lipase LIP-catalyzed enantioselective alcoholysis of the chloroacetate with 1-hexanol was much higher than that of the acetylating the alcohol with vinyl acetate.
引用
收藏
页码:194 / 196
页数:3
相关论文
共 15 条
[1]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299
[2]   LIPASE-CATALYZED ENANTIOSELECTIVE SYNTHESIS OF NAPHTHYL TRIFLUOROMETHYL CARBINOLS AND THEIR CORRESPONDING NON-FLUORINATED COUNTERPARTS [J].
GASPAR, J ;
GUERRERO, A .
TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :231-238
[3]  
HOREAU A, 1971, TETRAHEDRON LETT, V22, P1939
[4]   LIPASE-CATALYZED STEREOSELECTIVE ACYLATION OF [1,1'-BINAPHTHYL]-2,2'-DIOL AND DEACYLATION OF ITS ESTERS IN AN ORGANIC-SOLVENT [J].
INAGAKI, M ;
HIRATAKE, J ;
NISHIOKA, T ;
ODA, J .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1989, 53 (07) :1879-1884
[5]   PREPARATION AND LIPASE-CATALYZED OPTICAL RESOLUTION OF 2,2,2-TRIFLUORO-1-(NAPHTHYL)ETHANOLS [J].
KATO, K ;
KATAYAMA, M ;
GAUTAM, RK ;
FUJII, S ;
KIMOTO, H .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1995, 59 (02) :271-276
[6]   Optical resolution of 2,2,2-trifluoro-1-(9-phenanthryl)ethanol via enzymatic alcoholysis of its activated ester [J].
Kato, K ;
Katayama, M ;
Fujii, S ;
Fukaya, H ;
Kimoto, H .
JOURNAL OF FERMENTATION AND BIOENGINEERING, 1996, 81 (03) :206-211
[7]   LIPASE-CATALYZED OPTICAL RESOLUTION OF 2,2,2-TRIFLUORO-1-(INDOLE-3-)ETHANOLS IN ORGANIC-SOLVENTS [J].
KATO, K ;
KATAYAMA, M ;
GAUTAM, RK ;
FUJII, S ;
KIMOTO, H .
JOURNAL OF FERMENTATION AND BIOENGINEERING, 1994, 78 (01) :64-69
[8]   OPTICAL RESOLUTION OF 1-ARYLETHANOLS WITH A CONDENSED AROMATIC RING BY LIPASE FROM PSEUDOMONAS-AERUGINOSA [J].
KATO, K ;
KATAYAMA, M ;
FUJII, S ;
KIMOTO, H .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1995, 59 (11) :2178-2180
[9]  
KATO K, 1996, ANN M JAP SOC BIOSC, P237
[10]   ACYLATION OF ACTIVATED AROMATIC SUBSTRATES UNDER MILD CONDITIONS WITH (RCO)(2)O/ME(2)S/BF3 [J].
KISELYOV, AS ;
HARVEY, RG .
TETRAHEDRON LETTERS, 1995, 36 (23) :4005-4008