95310-87-5Relevant articles and documents
Enantioselective hydrolysis of diethyl 3-hydroxyglutarate to ethyl (S)-3-hydroxyglutarate by immobilized Candida antarctica lipase B
Dong, Hua-Ping,Wang, Ya-Jun,Zheng, Yu-Guo
, p. 90 - 94 (2010)
Optically pure ethyl (S)-3-hydroxyglutarate [(S)-3-EHG] is used as a key precursor for synthesis of a variety of pharmaceutically important compounds. In this work, we established an efficient procedure for enantioselectively hydrolyzing diethyl 3-hydroxyglutarate (3-DHG) to optically active (S)-3-EHG employing immobilized Candida antarctica lipase B (Novozym 435). Under the optimized conditions: pH 7.0, agitation speed 200 rpm, temperature 40 °C, 3-DHG concentration 0.15 mol L-1, and enzyme loading 7 g L -1, (S)-3-EHG was prepared in above 95% ee value and 98.5% yield, and the reaction was free from external mass transfer and intra-particle diffusion limitations and kinetically controlled. The inhibitions of substrate (3-DHG) and product (3-EHG) were excluded because both displayed no decline in activity at elevated concentrations within the given ranges. In addition, ethanol, a byproduct of the reaction, inhibited lipase B following an uncompetitive inhibition pattern. The kinetic constants were obtained through non-linear regression, with values of Vmax 1.29 mmol min-1 g -1, Km 0.06 mol L-1, and Ki 0.37 mol L-1, respectively.
A chemoenzymatic approach to the stereocontrolled synthesis of the C1-C11 fragment of (+)-peloruside A
Schoenherr, Heike,Mollitor, Jan,Schneider, Christoph
experimental part, p. 3908 - 3918 (2010/09/05)
A highly efficient and diastereoselective synthesis of the C1C11 fragment of the marine natural product (+)-peloruside A has been developed. Through enzymatic desymmetrization of diethyl 3-hydroxyglutarate with lipase B from Candida antarctica a large-sca
Bifunctional chiral synthons via biochemical methods. 5. Preparation of (S)-ethyl hydrogen-3-hydroxyglutarate, key intermediate to (R)-4-amino-3-hydroxybutyric acid and L-carnitine
Gopalan,Sih
, p. 5235 - 5238 (2007/10/02)
Microbial enantioselective hydrolysis of diethyl-3-hydroxyglutarate afforded (S)-ethyl hydrogen-3-hydroxyglutarate, which was transformed into (R)-4-amino-3-hydroxybutyric acid and L-carnitine, via a Curtius and Hunsdiecker rearrangement, respectively.