Lipases, Synthesis of Chiral Compounds, Aqueous and Organic Solvents

Abstract

Lipases are the most frequently applied enzymes in organic synthesis. This contribution covers basic biochemical properties of lipases, aspects of reaction systems, and choice of synthetic strategies. The use of lipases in the kinetic resolution of primary, secondary, and tertiary alcohols as well as other chiral compounds is covered. Finally, selected examples for the protein engineering of lipases are given.

Immobilization of lipases on hydrophobic supports: immobilization mechanism, advantages, problems, and solutions

“…As commented above, the attractiveness of lipases is caused by their specific mode of action, the so-called interfacial activation (see next section). In fact, the possibility of recognizing hydrophobic substrates and being active in bulk hydrophobic media, such as organic solvents, promoted the development of enzymology in what was called "nonconventional solvents" (Adlercreutz, 2008;Bornscheuer, 2010;Cao and Matsuda, 2016;Herbst et al, 2012;Kamal et al, 2013;Kumar et al, 2016;Roy et al, 2013;Salihu and Alam, 2015;Stepankova et al, 2013;Ueda, 2010;Wang et al, 2016;Zhen, 2005).…”

The 3D model of the lipase/acyltransferase from Candida parapsilosis, a tool for the elucidation of structural determinants in CAL-A lipase superfamily

“…are largely used biocatalysts in organic synthesis [1][2][3][4][5][6][7], but their use in the oleochemical industry for the production of fatty esters mostly relies on non-aqueous processes using hydrophobic solvents [8]. Even if lipases offer the well-known advantages of enzymatic processes, the development of greener processes is the next challenge for the improvement of biotechnological transformations of oils and fats.…”

Biotechnological relevance of the lipase A from Candida antarctica

“…Undoubtedly, CALB, an enzyme possessing 317 amino acids with a molecular weight of 33 kDa and a pI = 6, is the most used lipase in biotransformation [51,[108][109][110][111][112][113][114][115][116][117], especially as a commercially immobilized preparation (Novozym 435) in which the enzyme is immobilized onto a macroporous resin (Lewatit VP OC1600, poly-methyl methacrylate crosslinked with divinyl-benzene) [118]. However, CALA remains a very interesting enzyme, although CALA is not as frequently used as CALB in biotransformations for organic synthesis [91,117] it presents some very peculiar features which make it very attractive.…”