Desymmetrization of cbz-serinol catalyzed by crude pig pancreatic lipase reveals action of lipases with opposite enantioselectivity

Lipase preparations from pig pancreas are widely used in industrial production of fine chemicals and pharmaceuticals. In our attempts to synthesize enantiopure building blocks for production of iminocyclitols, we used a crude preparation of pig pancreatic lipase in acetylation of carboxybenzyl-2-ami...

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Bibliographic Details
Published in:Journal of molecular catalysis. B, Enzymatic Enzymatic, 2013-01, Vol.85-86, p.134-139
Main Authors: Jacobsen, Elisabeth Egholm, Lie, Aleksander, Frigstad, Marte Marie Hansen, el-Behairy, Mohammed Farrag, Ljones, Torbjørn, Wohlgemuth, Roland, Anthonsen, Thorleif
Format: Article
Language:English
Subjects:
(R)- and (S)-selective lipases
acetates
acetonitrile
acetylation
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Biotransformations
Carboxybenzyl-2-amino-1,3-propanediol
catalysts
catalytic activity
Crude PPL
drugs
enantiomers
Fundamental and applied biological sciences. Psychology
hydrolysis
Methods. Procedures. Technologies
monitoring
pancreas
phosphates
Pure PPL
solvents
swine
tetrahydrofuran
triacylglycerol lipase
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Summary:Lipase preparations from pig pancreas are widely used in industrial production of fine chemicals and pharmaceuticals. In our attempts to synthesize enantiopure building blocks for production of iminocyclitols, we used a crude preparation of pig pancreatic lipase in acetylation of carboxybenzyl-2-amino-1,3-propanediol (cbz-serinol) with vinyl acetate in tetrahydrofuran. The enantiomeric excess of the product monoester changed from (2S)-monoacetate to (2R)-monoacetate after prolonged reaction. By using vinyl acetate both as solvent and acyl donor only the (2R)-monoacetate was obtained. Purified enzyme preparation gave only the (2S)-monoacetate. It is likely that the crude enzyme preparation contains lipases with opposite stereoselectivity, acting at different rates in the desymmetrization reaction. The same enzyme preparation was used in hydrolysis of the diacetylated propanediol in phosphate buffer and acetonitrile as co-solvent. After 24h the (2S)-monoacetate was obtained in high enantiomeric excess. Our results show that monitoring the progress of biocatalyzed reactions are of utmost importance, in particular when crude enzyme preparations are used as catalysts.
ISSN:1381-1177
1873-3158
DOI:10.1016/j.molcatb.2012.09.007