114645-34-0Relevant academic research and scientific papers
Efficient preparation of both enantiomers of 3,3,3-trifluoro-2-hydroxy-2- methylpropanoic acid catalyzed by Shinella sp. R-6 and Arthrobacter sp. S-2
Fuhshuku, Ken-Ichi,Watanabe, Shunsuke,Nishii, Tetsuro,Ishii, Akihiro,Asano, Yasuhisa
, p. 115 - 119 (2014)
Several microorganisms that can enantioselectively hydrolyze 3,3,3-trifluoro-2-hydroxy-2-methylpropanamide have been isolated from soil samples. These strains were capable of growing in a medium containing 3,3,3-trifluoro-2-hydroxy-2-methylpropanamide as the sole nitrogen source. Among them, Shinella sp. R-6 was identified as a strain capable of exhibiting R-selective hydrolysis activity, while Arthrobacter sp. S-2 was capable of exhibiting S-selective hydrolysis activity. The preparation of both enantiomers of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid via the two-step whole-cell reaction was investigated using these two strains.
Selection, purification, characterisation, and cloning of a novel heat-stable stereo-specific amidase from Klebsiella oxytoca, and its application in the synthesis of enantiomerically pure (R)- and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acids and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide
Shaw, Nicholas M.,Brieden, Walter,De Riedmatten, Patricia,Roduit, Jean-Paul,Zimmermann, Bertin,Neumueller, Roman,Naughton, Andrew,Robins, Karen,Tinschert, Andreas,Schmid, Evelyne,Hischier, Marie-Louise,Venetz, Veronika,Werlen, Josef,Zimmermann, Thomas
, p. 497 - 504 (2002)
We isolated, characterised, and cloned an enantio-specific amidase from Klebsiella oxytoca and used it to resolve (R,S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide, giving (R)3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide. The (S)-amide could then be hydrolysed chemically to (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid. The process can therefore be adapted to produce both (R)-and (S)-enantiomers of 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid, or (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide. The biocatalytic step is part of a combined chemical and biocatalytic route that starts from ethyl trifluoroacetoacetate. The products typically have a purity of greater than 98% and ee values of essentially 100% after isolation. The process has been used to produce 100-g amounts of the (S)-acid, and successfully scaled up to produce 100-kg amounts of the (R)-acid, with the biotransformation carried out at the 1500-L scale.
α-TRIFLUOROMETHYL-α-HYDROXY CARBOXYLIC ACIDS
Soloshonok, V. A.,Gerus, I. I.,Yagupol'skii, Yu. L.,Kukhar', V. P.
, p. 1298 - 1303 (2007/10/02)
The methyl esters of α-trifluoromethyl-α-hydroxy carboxylic acids were obtained by the reaction of methyl trifluoropyruvate with organometallic reagents (Cd, Mg, Zn).The characteristic features of the reactions in relation to the nature of the alkylating agent were demonstrated.
