199177-61-2Relevant academic research and scientific papers
Enantioselective ring opening of epoxides with cyanide catalysed by halohydrin dehalogenases: A new approach to non-racemic β-hydroxy nitriles
Elenkov, Maja Majeric,Hauer, Bernhard,Janssen, Dick B.
, p. 579 - 585 (2006)
Halohydrin dehalogenases (HheA, HheB and HheC) were found to efficiently catalyse a carbon-carbon bond forming reaction between terminal aliphatic epoxides and cyanide, yielding β-hydroxy nitriles. With all three enzymes nucleophilic ring opening of epoxi
Efficient preparation of (R)-3-hydroxypentanenitrile with high enantiomeric excess by enzymatic reduction with subsequent enhancement of the optical purity by lipase-catalyzed ester hydrolysis
Kawano, Shigeru,Hasegawa, Junzo,Yasohara, Yoshihiko
, p. 1796 - 1798,3 (2012/12/11)
An efficient chemo-enzymatic procedure for the synthesis of (R)-3-hydroxypentanenitrile (1) with over 99% enantiomeric excess using two enzymatic reactions was successfully established. Initial enantioselective enzymatic reduction of 3-oxopentanenitrile with reductase S1 gave (R)-1 with an 81.5% ee which was then converted to (R)-1-(cyanomethyl) propyl n-butyrate (3b). Subsequent lipase-catalyzed enantioselective hydrolysis of 3b gave (R)-1 in a high yield with over 99% ee.
Efficient preparation of (R)-3-hydroxypentanenitrile with high enantiomeric excess by enzymatic reduction with subsequent enhancement of the optical purity by lipase-catalyzed ester hydrolysis
Kawano, Shigeru,Hasegawa, Junzo,Yasohara, Yoshihiko
, p. 1796 - 1798 (2013/01/14)
An efficient chemo-enzymatic procedure for the synthesis of (R)-3-hydroxypentanenitrile (1) with over 99% enantiomeric excess using two enzymatic reactions was successfully established. Initial enantioselective enzymatic reduction of 3-oxopentanenitrile with reductase S1 gave (R)-1 with an 81.5% ee which was then converted to (R)-1-(cyanomethyl) propyl n-butyrate (3b). Subsequent lipase-catalyzed enantioselective hydrolysis of 3b gave (R)-1 in a high yield with over 99% ee.
A rational design of phosphonium salt type ionic liquids for ionic liquid coated-lipase catalyzed reaction
Abe, Yoshikazu,Yoshiyama, Kazuhide,Yagi, Yusuke,Hayase, Shuichi,Kawatsura, Motoi,Itoh, Toshiyuki
experimental part, p. 1976 - 1980 (2011/02/23)
A rational design of phosphonium ionic liquid for ionic liquid coated-lipase (IL1-PS)-catalyzed reaction has been investigated, and very rapid transesterification of secondary alcohols accomplished when IL1-PS was used as catalyst in 2-methoxyethoxymethyl(tri-n-butyl)phosphonium bis(trifluoromethanesulfonyl)amide ([P444MEM][NTf2]) as solvent while perfect enantioselectivity was maintaining. Increased K cat value was suggested to be the most important factor in IL1-PS working the best in [P444MEM][NTf2] solvent. The Royal Society of Chemistry 2010.
Preparation of novel hydrophobic fluorine-substituted-alkyl sulfate ionic liquids and application as an efficient reaction medium for lipase-catalyzed reaction
Tsukada, Yasuhiro,Iwamoto, Kazuhisa,Furutani, Hiroyuki,Matsushita, Yuichi,Abe, Yoshikazu,Matsumoto, Kei,Monda, Keishi,Hayase, Shuichi,Kawatsura, Motoi,Itoh, Toshiyuki
, p. 1801 - 1804 (2007/10/03)
Various types of differently fluorinated-alkyl sulfate ionic liquids have been prepared; the hydrophobicity was dependent on the content ratio of the fluorine on the alkyl sulfate anion and 2,2,3,3,4,4,5,5-octafluoropentyl sulfate salts showed hydrophobic properties. Melting point and viscosity were also dependent on the fluorine contents of the anionic part, while conductivity was determined by the cationic part and not influenced by the fluorine contents. Efficient lipase-catalyzed transesterification was demonstrated using hydrophobic 1-butyl-3-methylimidazolim 2,2,3,3,4,4,5,5-octafluoropentyl sulfate ([bmim][C5F8]) as solvent.
Increased enantioselectivity and remarkable acceleration of lipase-catalyzed transesterification by using an imidazolium PEG-Alkyl sulfate ionic liquid
Itoh, Toshiyuki,Matsushita, Yuichi,Abe, Yoshikazu,Han, Shi-Hui,Wada, Shohei,Hayase, Shuichi,Kawatsura, Motoi,Takai, Shigeomi,Morimoto, Minoru,Hirose, Yoshihiko
, p. 9228 - 9237 (2007/10/03)
Several types of imidazolium salt ionic liquids were prepared derived from poly(oxyethylene)alkyl sulfate and used as an additive or coating material for lipase-catalyzed transesterification in an organic solvent. A remarkably increased enantioselectivity was obtained when the salt was added at 3-10 mol % versus substrate in the Burkholderia cepacia lipase (lipase PS-C)-catalyzed transesterification of 1-phe nylethanol by using vinyl acetate in diisopropyl ether or a hexane solvent system. In particular, a remarkable acceleration was accomplished by the ionic liquid coating with lipase PS in an iPr2O solvent system while maintaining excellent enantioselectivity; it reached approximately 500- to 1000-fold acceleration for some substrates with excellent enantioselectivity. A similar acceleration was also observed for IL1-coated Candida rugosa lipase. MALDITOF mass spectrometry experiments of the ionic-liquid-coated lipase PS suggest that ionic liquid binds with lipase protein.
