Candida cylindracea lipase organic solvents

Lara, P. V., and Park, E. Y. 2004. Potential application of waste activated bleaching earth on the production of fatty acid alkyl esters using Candida cylindracea lipase in organic solvent system. Enzyme and Microb. Technol., 34, 270-277. 

When Candida rugosa lipase (formerly named Candida cylindracea lipase) was immobilized on an epoxy-activated resin it became resistant against acetaldehyde. Due to this immunization it could be repeatedly employed for the enantioselective acylation of secondary alcohols with vinyl acetate in dry organic solvents (Scheme 2.7) [78]. 

Table 11.1-17. Lipase-catalyzed enantiotopos-differentiating acylation of prochiral acyclic diols in organic solvents (CCL Candida cylindracea lipase, PFL Pseudomonas fluorescens lipase, PPL pig pancreas lipase, CVL Chromobacterium viscosum lipase, PSL Pseudomonas sp. lipase, RJL Rhizomucorjavanicus lipase, ANL Aspergillus niger lipase, CAL Candida antarctica lipase, not specified, PCL Pseudomonas cepacia lipase, CRL Candida rugosa lipase).

Saponification of steroid esters can also be steered with Candida cylindracea lipase (CCL),272, 273]. This process occurs in the presence of octanol in organic solvents and is characterized by a pronounced stereospecificity and regioselectivity. Thus, the 3a-... 

It has also been demonstrated that lipases can be used to make amide bonds. Thus both porcine pancreatic lipase and Candida cylindracea lipase, in an organic solvent, proved to be effective catalysts for the synthesis of a wide range of dipeptides. 

Njar and Caspi [24] reported a mild procedure in neutral reaction conditions, which minimize the detrimental side reactions that often plague the traditional methodology, for the conversion of steroid esters into the corresponding alcohols via a lipase-catalyzed trans-esterification reaction with octanol in organic solvents. Among all of the lipases screened [porcine pancreas lipase (PPL), acetylcholinesterase, pepsin, and Candida cylindracea lipase (CCL)], CCL was revealed as best suited for this transesterification process. 

Ethyl small amounts (1-11%) of water-soluble organic solvents Candida cylindracea lipase from Sigma 168 35 31 >99 >100 90... 

The nature of the solvent plays an important role both in the yield and in the en-antioselectivity of the reaction. Thus, in Table 6B we can observe how the presence of CI4C reduces the yield and the enantiomeric excess in the resolution of esters of tri-methylsilyl methyl estem of rac-2-(6-methoxy-2-naphthyl)propionic acid with Candida cylindracea lipase [ICK)] another example is shown in Table 7B, where the synthesis of butyl esters of rac-ibuprofen is carried out in different organic media [98], obtaining the best results with solvents possessing log P (partition coefficient in the mixture n-octanol/ water) higher than 2.5. In the same table can be found another, similar example the esterification with methanol of rac-ibuprofen with lipase from C. cylindracea [108]. 

Enantioface-differentiating conjugate additions have also been performed using modified hydrolytic enzymes14. Thus, the addition of diethylamine to ethyl ( )-4,4,4-trifluoro-2-butenoatc in an organic solvent is catalyzed by a lipase from Candida cylindracea, a-chy-motrypsin or pig liver esterase to afford ethyl (-)-3-diethylamino-4,4,4-trifluorobutanoate in moderate yield (36-47%) and low optical purity (8-37% ee, as determined by l9F NMR using a chiral shift reagent)14. 

Optically pure inositol intermediates are very useful for synthesising D-myo-inositol 1,4,5-trisphosphate, which was found to be a second messenger. Ozaki et al [73] studied the resolution of racemic di-O-cylohexylidene-myo-inositol derivatives 17 and 18 by lipase-catalyzed esterification in organic solvents. Lipase from Candida cylindracea exclusively acetylates the hydroxyl group at C-4 or at C-5 of the D-enantiomer of 17 or 18, respectively. Around 100% e.e s of monoacetate products and unreacted starting compounds were obtained. The efficiency of the resolution is affected by the solvent, the most hydrophobic solvents ethyl ether and benzene being more effective than the water miscible solvents such as acetone, THF, and dioxane. 

A series of acetoxy derivatives of androstane were deacylated in organic solvents by several lipases. The most satisfactory results were obtained with lipase from Candida cylindracea (CCL) and Candida antarctica (CAL). In some derivatives, CCL and CAL showed an overwhelming regioselectivity toward the removal of the 3p- or the IT -acetyl group and three new steroid derivatives were obtained [31] through this approach (Fig. 17). 

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