Burkholderia cepacia lipases

R)-3-Phenoxybutanoic acid and the corresponding butyl (S)-ester were obtained by Burkholderia cepacia lipase-catalyzed enantioselective esterification of the racemic acid with 1-butanol in hexane containing anhydrous sodium sulfate to remove the water produced during the reaction (Figure 6.17) [64]. 

We investigated lipase-catalyzed acylation of 1-phenylethanol in the presence of various additives, in particular an E. additive using diisopropyl ether as solvent. Enhanced enantioselectivity was obtained when a BEG-hased novel IE, i.e., imidazolium polyoxyethylene(lO) cetyl sulfate, was added at 3-10 mol% vs. substrate in the Burkholderia cepacia lipase (hpase PS-C) catalyzed transesterification using vinyl acetate in diisopropyl ether or a hexane solvent system. ... 

Various cyclic esters have been subjected to hpase-catalyzed ring-opening polymerization. Lipase catalyzed the ring-opening polymerization of 4- to 17-membered non-substituted lactones.In 1993, it was first demonstrated that medium-size lactones, 8-valerolactone (8-VL, six-membered) and e-caprolactone (e-CL, seven-membered), were polymerized by lipases derived from Candida cylindracea, Burkholderia cepacia (lipase BC), Pseudomonas fluorescens (lipase PF), and porcine pancreas (PPL). °... 

Scheme 3 Reagents and conditions i) Burkholderia cepacia lipase, H2O, buffer pH 7, decane.

Burkholderia cepacia lipase (Amano PS) 2,2 -Bis(diphenylphosphino)-1,1 -binaphthyl Candida antarctica lipase B Diversity-oriented synthesis... 

Various lipases and esterases have been used for the enantioselective esterification of alcohols and hydrolysis of esters. For example, Burkholderia cepacia lipases (PS, Amano Enzyme Inc.) and Candida antarctica lipase (CAL, Novozymes) have been widely used for its wide substrate specificities, high activities and chemo, regio and enantioselectivities. Fundamentals and some selected applications are shown in this section. The origins and abbreviations of lipases introduced here are as follows. 

Yamauchi, A., Nagao, T., Watanabe, Y., Sumida, M., Kobayashi, T., and Shimada, Y. 2005. Purification of arachidonic acid from Mortierella single-cell oil by selective esterification with Burkholderia cepacia lipase. J. Am. Oil Chem. Soc., 82, 833-837. 

A general rule describing Burkholderia cepacia lipase (formerly called Pseudomonas cepacia lipase, PCL) catalysed conversions of primary alcohols with a chiral carbon in the / -position is depicted in Scheme 6.3. This rule, however, is only reliable if there are no oxygen substituents on the chiral carbon [14]. 

For the enantiopure production of human rhinovirus protease inhibitors scientists from Pfizer developed a kinetic resolution and recycling sequence (Scheme 6.14 A). The undesired enantiomer of the ester is hydrolysed and can be racemised under mild conditions with DBU. This enzymatic kinetic resolution plus racemisation replaced a significantly more expensive chemical approach [52]. An enzymatic kinetic resolution, in combination with an efficient chemically catalysed racemisation, is the basis for a chiral building block for the synthesis of Talsaclidine and Revatropate, neuromodulators acting on cholinergic muscarinic receptors (Scheme 6.14B). In this case a protease was the key to success [53]. Recently a kinetic resolution based on a Burkholderia cepacia lipase-catalysed reaction leading to the fungicide Mefenoxam was described [54]. Immobilisation of the enzyme ensured >20 cycles of use without loss of activity (Scheme 6.14 C). 

It is generally stated that biocatalysis in organic solvents refers to those systems in which the enzymes are suspended (or, sometimes, dissolved) in neat organic solvents in the presence of enough aqueous buffer (less than 5%) to ensure enzymatic activity. However, in the case of hydrolases water is also a substrate and it might be critical to find the water activity (a ) value to which the synthetic reaction (e.g. ester formation) can be optimized. Vahvety et al. [5] found that, in some cases, the activity of Candida rugosa lipase immobihzed on different supports showed the same activity profile versus o but a different absolute rate. With hpase from Burkholderia cepacia (lipase BC), previously known as lipase from Pseudomonas cepacia, and Candida antarctica lipase B (CALB) it was found that the enzyme activity profile versus o and even more the specific activity were dependent on the way the enzyme was freeze dried or immobihzed [6, 7]. A comparison of the transesterification activity of different forms of hpase BC or CALB can be observed in Tables 5.1 and 5.2, respectively. 

Kara P, Hanefeld U, Kanerva LT (2009) Immobilised burkholderia cepacia lipase in dry organic solvents and ionic liquids a comparison. Green Chem 11 250-256... 

Lundell K, Kurki T, Lindroos M et al (2005) Room temperature ionic liquids in the kinetic resolution of adrenaline-type aminoethanols by burkholderia cepacia lipase under normal and microwave conditions. Adv Syn Catal 347 1110-1118... 

Amano AH Pseudomonas cepacia lipase Amano AK Pseudomonas fluorescens lipase Amano PS Burkholderia cepacia lipase An Anisyl... 

The cycloisomerization of a- or (3-hydroxyallenes can also be carried out in water, for example with tetrachloroauric acid as catalyst. This system was used for the first example of a tandem lipase/gold-catalyzed transformation. The one-pot kinetic resolution/cycloisomerization of racemic allenic acetates with Burkholderia cepacia lipase (PS Amano SD Amano Enzyme USA Co., Ltd., Elgin, IL) and HAuCU afforded 2,5-dihydrofurans as well as unreacted starting material with 28-50% isolated yield and 86-98% ee (Scheme 4-96). The mutual tolerance of the Lewis-acidic gold catalyst with the Ixwis-basic lipase is maintained as long as low amounts of the former are used. 

Pseudomonas fluorescens lipase and Burkholderia cepacia lipase were the enzymes tested. In the case of phosphonate 146, the reverse procedure, i.e. the hydrolysis of the acetyl group, provides better results. Good yields (usually limited to 50% due to the kinetic conditions used) and ee values up to 92% were obtained for 144 and 145. 

Pseudomonas fluorescens lipase (lipase AK), Burkholderia cepacia lipase (lipase PS) and Candida antarctica lipase (CAL) were employed, with enol esters such as vinyl acetate, as acyl donors. The results with AK and PS lipases are summarised in Table 6.18. 

Kawakami, K., Y. Oda, and R. Takahashi. 2011. Application of a Burkholderia Cepacia Lipase-Immobilized Silica Monolith to Batch and Continuous Biodiesel Production with a Stoichiometric Mixture of Methanol and Crude Jatropha Oil. Biotechnology for Biofuels 4 (1) 42. 

Kawakami, K., Ueno, M., Takei, T., Oda, Y., and Takahashi, R. (2012) Application of a Burkholderia cepacia lipase-immobilized silica monolith micro-bioreactor to continuous-flow kinetic resolution for transesterification of (R,S)-l-phenylethanol. 

Cao, X., Yang, J., Shu, L, Yu, B., and Yan, Y. (2009) Improving esterification activity oi Burkholderia cepacia lipase encapsulated in silica by bioimprinting with substrate analogues. Process Biochem., 44 (2), 177-182. 

In combination with a Burkholderia cepacia lipase (PS-D I) for the kinetic resolution, various primary alcohols were converted into the corresponding enan-tiomerically pure esters in high yields (70-87%) and ee values ranging from 70% to 99% (17). The protocol was found applicable to both alkyl- and aiyl-substituted primary alcohols. 

Pseudomonas cepacia lipase (PCL) Sigma-Aldrich, Amano Enzyme Inc. (lipase PS SD) http //www.amano-enzyme. co.jp/aeu/index.html Nonrecombinant Synonyms Burkholderia cepacia lipase... 

PSL-C Burkholderia cepacia lipase ROA Raman optical activity... 

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