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Przemysłowe zastosowania lipaz w syntezie związków o wysokiej wartości dodanej – 85 lat katalizy enzymatycznej lipazami. Część 1

Borowiecki P.

Wiadomości Chemiczne

2015

[Z] 69, 5-6

391--430

Lipases (EC 3.1.1.3; triacylglycerol acylhydrolases) are the most commonly used enzymes in biotransformations of organic compounds. In living organisms lipases catalyze hydrolysis of higher fatty acid esters of glycerol, thus fulfill an essential function in metabolism of lipids (e.g. fats and oils) and lipoproteins. This year marks 125 years since J.R. Green has identified and described the first lipase isolated from germinated castor-oil beans (Ricinus communis L.) in the form of an extract showing hydrolytic properties. Plants, as well as bacteria are able to produce lipases what was reported in 1901 by Dutch scientist ‒ Christiaan Eijkman. Lipases are also produced by fungi, yeasts, and various organs of higher organisms. A strong foundation, which had a huge impact on the development of global lipase-mediated biotransformations was the discovery made in 1935 and described in Biochemistry Journal and Biochemische Zeitschrift by Polish biochemist- -enzymologist Ernest Alexander Sym (1893-1950) that these enzymes retain almost full catalytic activity even in nearly anhydrous organic solvents. This was exactly fifty years before Russian chemist Alexander Klibanov in 1985 described a lipase- -catalyzed reaction carried out in organic solvents. Since that moment, lipases have became extremely popular in both academic and industrial usage, nowadays being the most important among all biocatalysts used in biochemical processes carried out on an industrial scale. The purpose of this article is to provide a brief characterization of the two most widely used in industrial biotransformations lipases ‒ lipase B from Candida antarctica (CAL-B) and lipase from Burkholderia cepacia (BCL) ‒ and familiarize the readers with the issues of biotechnological processes catalyzed by them. The specifics of a range of industrial applications based on lipase catalysis, including the chemical, pharmaceutical, cosmetic and food industries are also discussed. Keywords:

Dwie dekady chemo-enzymatycznej reakcji Baeyera-Villigera

Drożdż A., Bielas R., Chrobok A.

Wiadomości Chemiczne

2014

[Z] 68, 11-12

1031--1048

The Baeyer–Villiger oxidation of ketones to lactones or esters is a reaction of significant interest in organic chemistry owing to very wide range of possible applications, e.g. in the synthesis of antibiotics, steroids, pheromones and monomers for polymerisation. The organic percarboxylic acids typically used as oxidants in these reactions are fairly expensive, often poorly stable and hazardous, and this consequently limits their commercial application. Therefore, the chemo-enzymatic approach appears to be a very attractive alternative. The paper presents literature reports concerning the application the use of lipase B from Candida antarctica in the chemo-enzymatic Baeyer-Villiger oxidation. It involves oxidation of long- or medium-chain carboxylic acids with H2O2 or urea hydrogen peroxide to generate in situ peracid which is later used to oxidise ketones to lactones.