Stereospecific hydrolysis of 3-(4-methoxyphenyl)glycidic ester in supercritical carbon dioxide by immobilized lipase

Abstract

In the hydrolysis of racemic 3-(4-methoxyphenyl)glycidic acid methyl ester by immobilized Mucor mlehei lipase in supercritical CO 2 the initial hydrolysis rate of the (2S,3R)-form was faster than the rate of the (2R,3S) -form. The stereoisomeric excess of the (2R,3S)-form reached 87 % at 53 % total conversion level. The water content of the reaction mixture and the initial concentration of the 3-(4-methoxyphenyl) glycidic acid methyl ester had no effect on isomeric purity. The reaction rate in supercritical CO 2 was considerably faster than in toluene/water -mixture.

Applied Biotransformations in Green Solvents

“…[7,100,101] There are several papers showing that lipases can operate in SCFs better than in organic solvents, [102][103][104] and describing how the use of scCO 2 has produced an improvement in enantioselectivity. [105][106][107] Many of these reported effects on lipases take place if the enzyme is immobilised on different surfaces, such as Celite, silica gel or polypropylene. [39,40,108] The employment of immobilisation techniques for industrial purposes is highly advantageous, due to the fact that this solid state confers robustness to the biocatalysts, and facilitates its recyclability.…”

“…They are commonly used in aqueous medium, while the employment in organic medium is still being studied 105. 106 However, Mori et al 41. 42 have described the use of scCO 2 or scCHF 3 in the transglycosylation of 1‐ p ‐nitrophenyl‐β ‐ D ‐galactopyranoside and 5‐phenylpentan‐1‐ol, catalysed by lipid‐coated β‐galactosidase from B. circulans (Table 2).…”

Production, purification, characterization, and applications of lipases

“…Hydrolysis is the favored reaction when there is excess water (Klibanov, 1997). Lipase-catalyzed reactions in supercritical solvents have been described (Rantakyla et al, 1996;Turner et al, 2001;King et al, 2001). …”

CO2‐Enabled Biomass Fractionation/Depolymerization: A Highly Versatile Pre‐Step for Downstream Processing

“… Stereospecific hydrolysis of 3‐(4‐methoxyphenyl)glycidic acid methyl ester by immobilized Mucor miehei lipase in Sc‐CO 2 …”