914929-68-3Relevant academic research and scientific papers
Enzyme-mediated enantioselective hydrolysis of soluble polymer-supported carboxylates
Okudomi, Masayuki,Ageishi, Kanpei,Yamada, Tomomi,Chihara, Naoka,Nakagawa, Takuya,Mizuochi, Katsumi,Matsumoto, Kazutsugu
, p. 8060 - 8067 (2010)
The enzyme-mediated enantioselective hydrolysis of water-soluble polymer-supported carboxylates is disclosed. The representative monomethoxy poly(ethylene glycol) (MPEG, av MW 5000)-supported substrate was synthesized by immobilization of (±)-1-phenylethanol onto the modified MPEG (MPEG/NH2) through an carboxylate linker with a succinate spacer. For the screening of the hydrolytic enzymes, the substrate was enantioselectively hydrolyzed by lipase from Candida antarctica (Novozym 435) in a mixed solvent (hexane/buffer=9/1) at 30 °C to afford the remaining (S)-substrate and the resulting (R)-alcohol (E value>200). The products were easily separated by a simple procedure without any laborious column chromatography. The substrate was hydrolyzed with NaOH in MeOH/H2O to afford the corresponding (S)-alcohol. We also found that the structure of the spacer between the MPEG moiety and the carboxylate linker strongly affected both the reactivity and enantioselectivity, and the substrate bearing a glutarate spacer gave the best result. Our procedure was applicable for the preparation of several optically active alcohols.
Enzyme-mediated enantioselective hydrolysis of dicarboxylic acid monoesters
Kataoka, Noriyuki,Okudomi, Masayuki,Chihara, Naoka,Matsumoto, Kazutsugu
, p. 615 - 621 (2013/02/23)
The enzyme-mediated highly enantioselective hydrolysis of dicarboxylic acid monoesters was investigated. The racemic substrates, which were prepared by coupling of the corresponding alcohols with dicarboxylic anhydrides, were enantioselectively hydrolyzed by lipase from Candida antarctica (Novozym 435) in a buffer at 30 °C. The products were easily separated by a simple extraction procedure without laborious column chromatography to afford both enantiomers of the alcohols. We then determined that the dicarboxylic acid monoesters were suitable alternative substrates for the preparation of optically active alcohols.
