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Lipase-catalyzed asymmetric hydrolysis of 3-phenylglycidic acid ester, the key intermediate in the synthesis of diltiazem hydrochloride


, : Lipase-catalyzed asymmetric hydrolysis of 3-phenylglycidic acid ester, the key intermediate in the synthesis of diltiazem hydrochloride. Journal Of Fermentation & Bioengineering. 75(2): 93-98

Asymmetric hydrolytic enzymes for trans-3-(4-methoxyphenyl)glycidic acid methyl ester ((+-)-MPGM), a key intermediate in the synthesis of diltiazem hydrochloride that is useful as a coronary vasodilator, were screened from 730 microorganisms. Among the microbial enzymes tested, Serratia marcescens lipase had the highest enantioselectivity (E = 135) for hydrolysis of (+-)-MPGM in a two-phase system using water (pH 8) and a water-immiscible solvent such as toluene. Resolution of (+-)-MPGM by S. marcescens lipase gave (2R, 3S)-3-(4-methoxyphenyl)glycidic acid methyl ester ((-)-MPGM) with a reaction yield of 48% and optical purity of gt 99.9% e.e. After the reaction, the emulsion of toluene and water was separated into two clear layers by the addition of sodium dodecyl sulfate. The crystalline ( sbd )-MPGM was isolated with a yield of over 43% and optical purity of 100% e.e. without column treatment. Diltiazem hydrochloride synthesis using asymmetric hydrolysis of (+-)-MPGM was found to be a more efficient process compared to the conventional chemical synthetic process. Some enzymatic characterizations on asymmetric in two-phases of organic solvent-water by S. marcescens lipase were investigated.

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DOI: 10.1016/0922-338x(93)90216-u


Other references

Gudden Helmut, 1972: The formation of the Upper Palatinate Cretaceous iron ore deposits as a function of flexure and fracture tectonics. Composition of ore, tectonics, ground water action, Germany.

Redgate, E.S.; Szechtman, H.; Fahringer, E.E., 1974: The effect of plasma cortisol concentration on the pituitary adrenal response elicited by electrical stimulation of the infundibular area of the awake unrestrained cat. Hormone Research 5(3): 173-181

Nielsen Niels, 1933: Gudmundur G. Bardarson; 24 Januar 1880-14 Marts 1933. Bulletin of the Geological Society of Denmark = Meddelelser fra Dansk Geologisk Forening: Pages 272-274. 1933.

Marsh, O.C., 1874: O. C. Marsh reviews the American fossil forms and their descent. New genera instituted are, Miohippu. O. C. Marsh reviews the American fossil forms and their descent. New genera instituted are, Miohippus (p. 249), Miocene, with three digits, and no anteorbital fossa; and Pliohippus (p. 252), Pliocene, with one digit and a large anteorbital fossa....

Yaguchi, S.; Matsumoto, M.; Date, R.; Harada, K.; Maeda, T.; Yamauchi, N.; Shigyo, M., 2014: Biochemical analyses of the antioxidative activity and chemical ingredients in eight different Allium alien monosomic addition lines. We measured the antioxidant contents and antioxidative activities in eight Allium fistulosum-shallot monosomic addition lines (MAL; FF+1A-FF+8A). The high antioxidative activity lines (FF+2A and FF+6A) showed high polyphenol accumulation. These ad...

Thompson, J.; Staby, G., 1983: How important is recutting flowers under water?. Florists' review, 172(4456): 18

Carper, M.J.; Potteiger, J.A.; Randall, J.C.; Jacobsen, D.J.; Hulver, M.W.; Thyfault, J.P., 2001: Lower leg anterior compartment pressure response prior to, during, and following chronic creatine supplementation. Medicine & Science in Sports & Exercise 33(5 Supplement): S207, May

Heisel, C., 1981: Determination of nutrient uptake by greenhouse-grown roses. In an 8-year study cv. Super Star roses were grown in hydroponic culture using a perlite/gravel mixture. The nutrient solution used was Wopil (1:0.44:1.33) and in some cases it was supplemented with NH4NO3 + K2SO4. The stronger the nutrient soluti...

Shin K.J.; Lee G.S.; Paek B.H.; Kim K.S., 1988: Effect of feeding ammoniated rice straw and concentrate level on daily gain feed intake and feed efficiency of korean native bulls. The study was carried out to evaluate the effect of feeding anhydrous ammonia treated rice straw (NH3-RS) with two different levels of concentrate on daily gain, feed consumption and feed efficiency. Rice straw (RS) was treated with 30g NH3/kg RS...

Parija, S.C.; Shivaprakash, M.R.; Jayakeerthi, S.R., 2003: Evaluation of lacto-phenol cotton blue (LPCB) for detection of Cryptosporidium, Cyclospora and Isospora in the wet mount preparation of stool. Lacto-phenol cotton blue (LPCB) was found to be a useful stain for detection of Cyclospora and Isospora oocysts in direct wet mounts of stool. LPCB stained these parasites blue, and differentiated their internal structures clearly, thereby facilit...