96894-63-2Relevant articles and documents
Enzymes in Organic Synthesis. 39. Preparations of Chiral Cyclic Acid-Esters and Bicyclic Lactones via Stereoselective Pig Liver Esterase Catalyzed Hydrolyses of Cyclic Meso Diesters
Sabbioni, Gabriele,Jones, J. Bryan
, p. 4565 - 4570 (1987)
Pig liver esterase catalyzed hydrolyses of meso-dimethyl cyclopropane-, cyclobutane-, and cyclohexane-1,2-dicarboxylates are enantiotopically specific, giving acid-ester products that are readily converted into γ-lactones of > 97percent ee that are of value as chiral synthons.There is a dramatic change of stereospecificity on going from the cyclopropane and cyclobutane diesters to the cyclohexane substrate, with the cyclopentane diester hydrolysis representing the changeover point within the series.This reversal of enzyme stereospecificity is explicable in terms of a twobinding-pocket active-site model.Hydrolyses of dimethyl oxirane-2,3-dicarboxylate and of cyclopropane-1,2-diacetates are also stereoselective, giving product ee's up to 30-70percent.
A Study of Stereoselective Hydrolysis of Symmetrical Diesters with Pig Liver Esterase
Mohr, Peter,Waespe-Sarcevic, Nada,Tamm, Christoph,Gawronska, Krystyna,Gawronsky, Jacek K.
, p. 2501 - 2511 (2007/10/02)
Pig liver esterase (PLE) catalyzed hydrolysis of dimethyl esters of symmetrical dicarboxylic acids, including meso-diacids, cis-1,2-cycloalkanedicarboxylic acids, and diacids with a prochiral center, was studied with 14 substrates.The products of these stereoselective hydrolyses are chiral monoesters of dicarboxylic acids, with an enantiomeric excess (e.e.) from 10percent to 100percent.Some of these optically active monoesters are valuable synthons in natural products synthesis.An additivity pattern of α- and β-substituents with the glutaric esters on the stereoselectivity of enzymatic hydrolysis was observed.Analysis of the experimental results leads to a model of enzyme stereoselectivity of diester hydrolysis in which the substitution pattern at α- and β-C-atoms is found to determine the absolute configuration of the resulting monoester.