Enantioselective hydrolysis of cyclic carbonates by porcine pancreatic lipase to afford optically active 1,2-alkanediols

1993 ◽  
Vol 15 (10) ◽  
pp. 1039-1042 ◽  
Author(s):  
Masatoshi Kawashima ◽  
Yuko Horikawa
Keyword(s):  
Pancreatic Lipase ◽  
Optically Active ◽  
Enantioselective Hydrolysis ◽  
Porcine Pancreatic Lipase ◽  
Cyclic Carbonates ◽  
Hydrolysis Of

Enzymes in organic synthesis. 36. Synthesis of optically active civet constituent from an enzyme-generated chiral synthon

1987 ◽  
Vol 65 (4) ◽  
pp. 704-707 ◽  
Author(s):  
J. Bryan Jones ◽  
R. Scott Hinks
Keyword(s):  
Acetic Acid ◽  
Organic Synthesis ◽  
Pancreatic Lipase ◽  
Optically Active ◽  
Starting Material ◽  
Porcine Pancreatic Lipase ◽  
Hydrolysis Of ◽  
Enzymes In Organic Synthesis ◽  
Chiral Synthon

A synthesis of the civet constituent, (+)-(S,S)-(cis-6-methyltetrahydropyran-2-yl)acetic acid, is described, in which the key stereochemistry of the chiral starting material is set by an enantiotopically selective, porcine pancreatic lipase-catalyzed, hydrolysis of a meso diester.

Recent Studies on the Application of Enzymes in the Synthesis of Polyesters

1990 ◽  
Vol 218 ◽  
Author(s):  
Cary J. Morrow ◽  
Eugenia M. Brazwell ◽  
Dianela Filos ◽  
Juanita Mercure ◽  
Rosemary Romero ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Ambient Temperature ◽  
Organic Solvents ◽  
Pancreatic Lipase ◽  
Bound Water ◽  
Optically Active ◽  
Porcine Pancreatic Lipase ◽  
Dibenzyl Ether ◽  
High Boiling Solvent ◽  
Hydrolysis Of

AbstractEnzyme-catalyzed preparation of polymers offers several potentially valuable advantages over the usual polymerization procedures. This paper summarizes our successful use of lipase-catalyzed polycondensations to prepare both a series of achiral [AA-BB]x polyesters from bis(2,2,2- trichloroethyl) alkanedioates and diols and of an optically active, epoxy-substituted polyester having a stereochemical purity estimated to be greater than 96%, from racemic bis(2,2,2-trichloroethyl) trans-3,4-epoxyhexanedioate and 1,4-butanediol. All of the reactions were carried out at ambient temperature in anhydrous, low to intermediate polarity, organic solvents such as ether, THF, 2-ethoxyethyl ether, dibenzyl ether, o-dichlorobenzene, or methylene choride, using porcine pancreatic lipase (PPL) as the catalyst. The molecular weight achieved by the polycondensation is limited by accumulation of the trihaloethanol that forms as the reaction progresses, probably because it frees enzyme-bound water permitting hydrolysis of the polymer to occur. This problem has been alleviated by using a high boiling solvent and removing the alcohol by placing the re'action mixture under vacuum.

Porcine Pancreatic Lipase Catalyzed Enantioselective Hydrolysis of Esters ofN-Protected Unusual Amino Acids

1989 ◽  
Vol 18 (12) ◽  
pp. 2219-2222 ◽  
Author(s):  
Toshifumi Miyazawa ◽  
Hitoshi Iwanaga ◽  
Shinichi Ueji ◽  
Takashi Yamada ◽  
Shigeru Kuwata
Keyword(s):  
Amino Acids ◽  
Pancreatic Lipase ◽  
Enantioselective Hydrolysis ◽  
Porcine Pancreatic Lipase ◽  
Unusual Amino Acids ◽  
Hydrolysis Of Esters ◽  
Hydrolysis Of
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