Lipases chromobacterium viscosum lipase

Chromobacterium viscosum lipase, cyclohexane, vinyl acetate, THF, 40°." Cleavage... 

Under comparable conditions, the reaction rates of the octyl decanoate synthesis by chromobacterium viscosum lipase in AOT-based microemulsions or immobihzed in AOT-based organogels were similar [286,287],... 

A Chromobacterium viscosum lipase is microencapsulated in AOT reversed micelles in isooctane with a Wo=24 and used in the controlled hydrolysis of 50 mM triolein at pH 7.0 and 35°C, in a continous stirred membrane reactor, with a flow rate of 1 l.min 1 Design the reactor in order to achieve 95% of conversion. 

Lipase-catalyzed intermolecular condensation of diacids with diols results in a mixture of macrocyclic lactones and linear oligomers. Interestingly, the reaction temperature has a strong effect on the product distribution. The condensation of a,CO-diacids with a,(0-dialcohols catalyzed by Candida cyiindracea or Pseudomonas sp. lipases leads to macrocyclic lactones at temperatures between 55 and 75°C (91), but at lower temperatures (<45°C) the formation of oligomeric esters predominates. Optically active trimers and pentamers can be produced at room temperature by PPL or Chromobacterium viscosum lipase-catalyzed condensation of bis (2,2,2-trichloroethyl) (+)-3-methyladipate and 1,6-hexanediol (92). 

A number of steroids have been regioselectively acylated in a similar manner (99,104). Chromobacterium viscosum lipase esterifies 5a-androstane-3p,17p-diol [571-20-0] (75) with 2,2,2-trifluoroethyl butyrate in acetone with high selectivity. The lipase acylates exclusively the hydroxy group in the 3-position giving the 3p-(monobutyryl ester) of (75) in 83% yield. In contrast, bacillus subtilis protease (subtilisin) displays a marked preference for the C-17 hydroxyl. Candida cylindracea lipase (CCL) suspended in anhydrous benzene regioselectively acylates the 3a-hydroxyl group of several bile acid derivatives (104). 

Enantioselective enzymatic transesterifications have been successfully used for the synthesis of optically active silanes with the silicon atom as the center of chirality. As shown in Scheme 20, the prochiral bis(hydroxymethyl)silanes 86 and 88 were transformed into the corresponding chiral dextrorotatory isobutyrates (+)-87 and (+)-89, respectively, using Candida cylindracea lipase (CCL, E.C. 3.1.1.3) as the biocatalyst73. For these bioconversions, methyl isobutyrate was used as solvent and acylation agent. When using acetoxime isobutyrate as the acylation agent and Chromobacterium viscosum lipase (CVL ... 

The 5 -(-)-2-cyclohexy 1-1,3-propanediol monoacetate (24) and the S-( )-2-phenyl-1,3-propanediol monoacetate (25) are key chiral intermediates for the chemoenzymatic synthesis of Monopril (26) (Fig. 10), a new antihypertensive drug which acts as an ACE inhibitor. The asymmetric hydrolysis of 2-cyclohexyl-1,3-propanediol diacetate (27) and 2-phenyl-1,3-propanediol diacetate (28) to the corresponding S-( - )-monoacetate (24) and S-( )-monoacetate (25) by porcine pancreatic lipase (PPL) and Chromobacterium viscosum lipase have been demon-... 

Another example using a prochiral acetate and asymmetric hydrolysis was described by the Bristol-Myers Squibb group for an intermediate in the synthesis of Monopril (fosinopril sodium) (41), an ACE inhibitor (Scheme 19.23). The prochiral substrate 42 was hydrolyzed both when R = phenyl or cyclohexyl to the corresponding (S)-(-)-monoacetate 43. The reaction was carried out in a 10% toluene biphasic system with either PPL or Chromobacterium viscosum lipase. The cyclohexyl monoacetate was obtained in 90% yield with an optical purity of 99.8%.107 195... 

There are also several reports on highly regioselective transesterification of various steroid derivatives, one example being displayed in eq 14 in which butyration occurred exclusively at the 3p-hydroxyl group by Chromobacterium viscosum lipase (CVL). Opposite regioselectivity toward the 17p-hydroxyl group was observed with subtilisin protease. ... 

Table 11.1-11. Lipase-catalyzed enantiotopos-differentiating hydrolysis of prochiral cyclic diol dialkanoates in aqueous solution (CCL Candida cylindracea lipase, PFL Pseudomonas jiuorescens lipase, MML Mucor miehei lipase, CVL Chromobacterium viscosum lipase, PPL pig pancreas lipase, MJL Mucor javanicus lipase, RSL Rhizopus sp. lipase, PCL Pseudomonas cepacia lipase, CCL, Ceotricum candidum lipase, ANL Aspergillus niger lipase, FSPC Fusarium solani pisi cutinase, CRL Candida rugosa lipase, CAL-B Candida antarctica B lipase, LIP Pseudomonas sp. lipase-Toyobo, RDL Rhizopus delemar lipase, MSL Mucor sp. lipase, CAL Candida antarctica lipase, not specified).

Table 11.1-12. Lipase-catalyzed enantiotopos-differentiating hydrolysis of prochiral acyclic and cyclic dicarboxylic acid diesters in aqueous solution (CCL Candida cylindracea lipase, PPL pig pancreas lipase, PSL Pseudomonas sp. lipase, CVL Chromobacterium viscosum lipase,...

NMR self-diffusion measurements indicated that all microemulsions consisted of closed water droplets and that the structure did not change much during the course of reaction. Hydrolysis was fast in microemulsions based on branched-chain anionic and nonionic surfactants but very slow when a branched cationic or a linear nonionic surfactant was employed (Fig. 11). The cationic surfactant was found to form aggregates with the enzyme. No such interactions were detected with the other surfactants. The straight-chain, but not the branched-chain, alcohol ethoxylate was a substrate for the enzyme. A slow rate of triglyceride hydrolysis for a Ci2E4-based microemulsion compared with formulations based on the anionic surfactant AOT [61,63] and the cationic surfactant cetyltrimethylammonium bromide (CTAB) [63] was observed in other cases also. Evidently, this type of lipase-catalyzed reaction should preferably be performed in a microemulsion based on an anionic or branched nonionic surfactant. Nonlipolytic enzymes such as cholesterol oxidase seem to function well in microemulsions based on straight-chain nonionic surfactants, however [64]. CTAB was reported to cause slow inactivation of different types of enzymes [62,64,65] and also, in the case of Chromobacterium viscosum lipase [66], to provide excellent stability. 

Zaman MM, HayashiY.Talukder MMR, KawanishiT. Enhanced activity and stability of Chromobacterium viscosum lipase in AOT reverse micellar systems by pretreatment with acetone. J Mol Catal B... 

Chromobacterium viscosum lipase on polyethylene glycol immobilized... 

The preparation and periodate oxidation of C-6 oxycellulose have been studied and a conformational interpretation of hemiacetal stability presented. Cellulose acylated with palmitoyl chloride provides a suitable affinity matrix for the purification of Chromobacterium viscosum lipase. ... 

Rodrigues, A. R., J. M. S. Cabral, and M. A. Taipa. 2002. Immobilization of Chromobacterium Viscosum Lipase on Eudragit S-100 Coupling, Characterization and Kinetic Application in Organic and Biphasic Media. Enzyme and Microbial Technology 31 (1-2) 133-141. 

Many lipases, such as porcine pancreatic lipase (PPL), Candida cylindracea lipase (CCL), Chromobacterium viscosum lipase (CVL), Candida antarctica lipase (CAL), Candida antarctica lipase B (CALB, Novozyme-435), polyethylene glycol (PEG)-modified Pseudomonas fluorescens lipase (PEL), Pseudomonas cepacia lipase (PsCL),... 

Yamada, Y, Kuboi, R., Komasawa, 1.1993. Increased activity of Chromobacterium viscosum lipase in aerosol OT reverse micelles in the presence of nonionic surfactants. Biotechnol. Prog. 9, 468-472. 

Chang, P.S., Rhee, J.S., Kim, J.-J. 1991. Continuous glycerolysis of olive oil by Chromobacterium viscosum lipase immobilized on liposome in reversed micelles. Biotechnol. Bioeng. 38,1159-1165. 

Jenta, T.R.-J., Batts, G., Rees, G.D., Robinson, B.H. 1997. Biocatalysis using gelatine microemulsion-based organogels containing immobilized Chromobacterium viscosum lipase. Biotech. Bioeng. 53, 121-131. 

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