Enzymes in organic synthesis. 33. Stereoselective pig liver esterase-catalyzed hydrolyses of meso cyclopentyl-, tetrahydrofuranyl-, and tetrahydrothiophenyl-1,3-diesters

1985 ◽  
Vol 63 (2) ◽  
pp. 452-456 ◽  
Author(s):  
J. Bryan Jones ◽  
R. Scott Hinks ◽  
Philip G. Hultin
Keyword(s):  
Organic Synthesis ◽  
Absolute Configuration ◽  
Enantiomeric Excess ◽  
Membered Ring ◽  
Pig Liver ◽  
Pig Liver Esterase ◽  
Preparative Scale ◽  
Liver Esterase ◽  
The Absolute ◽  
Enzymes In Organic Synthesis

Preparative-scale pig liver esterase-catalyzed hydrolyses of five-membered ring meso-1,3-diesters are enantiotopically selective. While pro-S enantiotopic selectivity is exhibited in each case, the absolute configuration sense of the hydrolysis in the cyclopentyl series is opposite to that of both the tetrahydrofuranyl and tetrahydrothiophenyl diesters. The enantiomeric excess levels induced are in the 34–46% range.

Enzymes in organic synthesis. 44. Stereoselective pig liver esterase-catalyzed hydrolyses of 3-substituted glutarate diesters of compactin-synthon interest

1988 ◽  
Vol 66 (6) ◽  
pp. 1422-1424 ◽  
Author(s):  
Lister K.-P. Lam ◽  
J. Bryan Jones
Keyword(s):  
Organic Synthesis ◽  
Acid Ester ◽  
Enantiomeric Excess ◽  
Pig Liver ◽  
Pig Liver Esterase ◽  
Liver Esterase ◽  
Enzymes In Organic Synthesis

Pig liver esterase-catalyzed hydrolyses of dimethyl 3-hydroxy-, 3-methoxyethoxymethoxy-, and 3-benzyloxyglutarates occur with enantiotopic stereoselectivity to give the corresponding acid-ester products of 16–40% enantiomeric excess (ee). The results also provide another example of reversal of PLE-stereoselectivity.

Enzymes in organic synthesis. 40. Evaluation of the enantioselectivity of the pig liver esterase catalyzed hydrolyses of racemic piperidine carboxylic acid esters

1987 ◽  
Vol 65 (12) ◽  
pp. 2722-2726 ◽  
Author(s):  
Eric J. Toone ◽  
J. Bryan Jones
Keyword(s):  
Carboxylic Acid ◽  
Organic Synthesis ◽  
Enantiomeric Excess ◽  
Pig Liver ◽  
Pig Liver Esterase ◽  
Liver Esterase ◽  
Hydrolysis Of ◽  
Enzymes In Organic Synthesis ◽  
Acid Esters

Pig liver esterase (PLE) catalyzed hydrolysis of racemic piperidine esters proceeds enantioselectively to give product acids and recovered esters in 0–47% enantiomeric excess.

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