Stereoselective enzymatic hydrolysis of 2-cyclohexyl-and 2-phenyl-1,3-propanediol diacetate in biphasic systems

A key intermediate (S(-)2-cyclohexyl-1,3-propanediol monoacetate) was made with high optical purity for the total synthesis of a new angiotensin converting enzyme inhibitor, Fosinopril. The stereoselective hydrolysis of 2-cyclohexyl-1,3-propanediol diacetate (I) and 2-phenyl-1,3-propanediol diacetat...

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Bibliographic Details
Published in:Applied microbiology and biotechnology 1990-10, Vol.34 (1), p.10-14
Main Authors: PATEL, R. N, ROBISON, R. S, SZARKA, L. J
Format: Article
Language:English
Subjects:
2-cyclohexyl-1,3-propanediol diacetate
2-phenyl-1,3-propanediol diacetate
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Fundamental and applied biological sciences. Psychology
Methods. Procedures. Technologies
triacylglycerol lipase
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Summary:A key intermediate (S(-)2-cyclohexyl-1,3-propanediol monoacetate) was made with high optical purity for the total synthesis of a new angiotensin converting enzyme inhibitor, Fosinopril. The stereoselective hydrolysis of 2-cyclohexyl-1,3-propanediol diacetate (I) and 2-phenyl-1,3-propanediol diacetate (II) was carried out with lipases. Among various lipases evaluated, only porcine pancreatic lipase (PPL) and Chromobacterium viscosum lipase demonstrated efficient conversion and gave the desired enantiomer of monoacetate. In aqueous solution, the desired S(-)monoacetate exhibited an optical purity of 65%-80% (30%-60% enantiomeric excess (e.e.)). However, when the same reactions were conducted in a biphasic system, the product S(-)monoacetate exhibited an optical purity of 99%-100% (98%-100% e.e.).
ISSN:0175-7598
1432-0614
DOI:10.1007/BF00170915