Lipases in organic synthesis

Lipases (or triacylglycerol ester hydrolases) are enzymes belonging to the serine hydrolase family that catalyse hydrolysis of fats and oils to free fatty acids and 

Separation of Enantiomers Synthetic Methods, First Edition. Edited by Matthew Todd. 

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Haraldsson, G. The application of lipases in organic synthesis in The chemistry of acid derivatives edited by S. Patai, John Wiley Sons Ltd 1992, vol. 2, 1396-1467. 

Gotor-FemSndez, V. and Gotor, V. (2007) Use of lipases in organic synthesis, in Industrial Enzymes Structure, Function and Application (eds ). Polaina and A.P. MacCabe), Springer, Dordrech, The Netherland, Chapter 18. 

Anderson EM, Karin M, Kirk O (1998) One biocatalyst—many applications the use of Candida antarctica B-lipase in organic synthesis. Biocatal Biotransf 16 181-204... 

Further information about general properties, structural features, and applications of lipases in organic synthesis is available in a review (Schmid and Verger, 1998), a book chapter (Kazlauskas and Bornscheuer, 1998), and a book (Bomscheuer and Kazlauskas, 1999). 

Hydroperoxides play an important role as oxidants in organic synthesis [56-58]. Although several methods are available for the preparation of racemic hydroperoxides, no convenient method of a broad scope was until recently [59] known for the synthesis of optically active hydroperoxides. Such peroxides have potential as oxidants in the asymmetric oxidation of organic substrates, currently a subject of intensive investigations in synthetic organic chemistry [60, 61]. The application of lipoxygenase [62-65] and lipases [66,67] facilitated the preparation of optically active hydroperoxides by enzymes for the first time. 

Oxidoreductases are, after lipases, the second most-used kinds of biocatalysts in organic synthesis. Two main processes have been reported using this type of enzymes-bioreduction of carbonyl groups [39] and biohydroxylation of non-activated substrates [40]. However, in recent few years other processes such as deracemization of amines or alcohols [41] and enzymatic Baeyer-Villiger reactions of ketones and aldehydes [42] are being used with great utility in asymmetric synthesis. 

Lipases play an important role in organic synthesis and also in flavour biotechnology. Pig pancreatic extract and especially many microbial lipases are used for ester hydrolysis, esterification (alcohol and acid), transesterification (ester and... 

Hydrolases are widely used enzymes in organic synthesis, with most applications concentrating on lipases and esterases. This chapter discloses the possibilities of asymmetric accesses to chiral building blocks for the synthesis of natural products... 

Kinetic resolutions in general are regularly applied in organic synthesis. Since enzymes are highly attractive for asymmetric synthesis, various types of biocatalysts have been used in enzymatic (dynamic) kinetic resolutions, but the focus will remain on lipase- and esterase-mediated resolutions as the most common tools in early steps of natural product syntheses. 

Lipases (triacylglycerol acyl hydrolases, EC 3.1.1.3), have been well established as a valuable catalyst in organic synthesis.12 They are usually distinguished from carboxyl esterases (EC 3.1.1.1) by their substrate spectra, i.e. esterases prefer water soluble substrates and lipases show significantly higher activity towards their natural substrates,... 

Secondary alcohols are by far the most frequently used targets in lipase-catalyzed resolutions. This is due to their importance in organic synthesis but also that lipases usually show much higher enantioselectivity in resolutions compared to primary and tertiary alcohols. 

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