Optimizing lipase activity, enantioselectivity, and stability with medium engineering and immobilization for ?-blocker synthesis

Mohapatra, Satish; Hsu, Jong-Ping

doi:10.1002/(sici)1097-0290(19990720)64:2<213::aid-bit10>3.0.co;2-u

Cited by 34 publications

(14 citation statements)

References 20 publications

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“…For example, the denaturant solvents, such as dimethylsulfoxide, were added to organic solvents and the yield of the product catalyzed by lipase was improved. [9][10][11] The industrial demands accelerated only in the aspect of the ester synthesis or ester exchange processes catalyzed by lipase.…”

mentioning

confidence: 99%

Polar Organic Solvent Added to an Aqueous Solution Changes Hydrolytic Property of Lipase

Tsuzuki

Nagao

2003

Bioscience, Biotechnology, and Biochemistry

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mentioning

confidence: 99%

Polar Organic Solvent Added to an Aqueous Solution Changes Hydrolytic Property of Lipase

Tsuzuki

Nagao

2003

Bioscience, Biotechnology, and Biochemistry

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“…However, such solvents usually strip the essential water off the enzyme molecules and thus inactivate the biocatalysts, which limits the application of enzymatic procedures in these areas [24]. Moreover, the selectivity, such as regioselectivity [25], enantioselectivity [26] and substrate selectivity [27], could be manipulated by the reaction medium.…”

Section: Resultsmentioning

confidence: 99%

Efficient regioselective synthesis of 3′‐O‐crotonylfloxuridine catalysed by Pseudomonas cepacia lipase

Zhao

Zong

2009

Biotech and App Biochem

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Pseudomonas cepacia lipase-catalysed preferential acylation of the secondary hydroxy group of FUdR (floxuridine) with vinyl crotonate was carried out in spite of the presence of the primary hydroxy group, and 3'-O-crotonylfloxuridine was prepared successfully for the first time. The isomerization of the double bond of crotonate, which occurs in conventional organic synthesis, could be effectively avoided during the enzymatic acylation. The effects of some key factors such as reaction medium, initial a(w) (water activity), molar ratio of vinyl crotonate to FUdR, FUdR concentration and reaction temperature on the reaction were examined. Under the optimized reaction conditions, the initial reaction rate, substrate conversion and 3'-regioselectivity of the reaction were as high as 24 mM/h, 98% and 85% respectively.

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“…Complete solubilization of the substrate in water by addition of polar organic solvents was reported to reduce the catalytic property of lipase which led to the conclusion that the oil/water interfacial surface plays an important role in the resultant kinetic properties of the enzyme. Another report by these authors concerned suitable medium engineering and enzyme immobilization and PEG modification to obtain the desired high optical purity of products [32]. They used a few different polar organic solvents (acetone, DMSO, 1,4-dioxane, DMF, 1-propanol, tetrahydrofuran).…”

Section: A Chlorohydrinsmentioning

confidence: 99%

Biocatalytic Approaches to Optically Active β-Blockers

Żelaszczyk¹,

Kieć‐Kononowicz

2007

CMC

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Beta-blockers are a very important group of drugs widely used for the treatment of cardiovascular diseases. All aryloxyaminopropanols are chiral and show different stereoselectivity in their pharmacodynamic and pharmacokinetic properties for each enantiomer. The more potent beta-adrenoceptor blocking activity is generally associated with (S)-enantiomers. Most beta-blocking agents are sold as racemates although (R)-enantiomers not only show in some cases lack of activity but might be responsible for undesirable effects. Among reports on the direct enzymatic resolution of the most representative beta-blocker propranolol, the most interesting is N-acetylation method with commercially available lipases to yield (S)-N-acetylpropranolol. Another type of the one-step (S)-isomer biocatalytic preparation from racemic mixture of propranolol is the biodegradation with the fungus. Biocatalytic methods of obtaining homochiral beta-blockers that are focused on production of versatile precursors are widely described in literature. The strategies based on the use of glycidol and derivatives as C-3 synthones have been shown to be extremely useful for the introduction of the 2-propanol chain on the aromatic system. Halohydrins are the established intermediates in the preparation of optically active beta-blockers. Its resolution by esterhydrolases has been used as a standard alternative in preparation of the homochiral propranolol. Additionally, the enzymatic resolution of the following intermediates was reported: 1-azido-3-aryloxy-2-propanols, 4-(1-aryloxy)-3-hydroxybutyric acid esters, glycerol and cyanohydrin derivatives. However, even the highly enantioselective lipase-catalyzed process can only provide 50% of the starting racemate in an optically active form. An alternative method such as a reduction of a prochiral ketone by various strains of yeast might quantitatively provide an enantiomeric product with a yield greater than 50%. The reported substrates for microbial reductions were: 1-halo-aryloxypropan-2-ones and 1-acetoxy-aryloxypropan-2-ones.

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Optimizing lipase activity, enantioselectivity, and stability with medium engineering and immobilization for ?-blocker synthesis

Cited by 34 publications

References 20 publications

Polar Organic Solvent Added to an Aqueous Solution Changes Hydrolytic Property of Lipase

Polar Organic Solvent Added to an Aqueous Solution Changes Hydrolytic Property of Lipase

Efficient regioselective synthesis of 3′‐O‐crotonylfloxuridine catalysed by Pseudomonas cepacia lipase

Biocatalytic Approaches to Optically Active β-Blockers

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Optimizing lipase activity, enantioselectivity, and stability with medium engineering and immobilization for ?-blocker synthesis

Cited by 34 publications

References 20 publications

Polar Organic Solvent Added to an Aqueous Solution Changes Hydrolytic Property of Lipase

Polar Organic Solvent Added to an Aqueous Solution Changes Hydrolytic Property of Lipase

Efficient regioselective synthesis of 3′‐O‐crotonylfloxuridine catalysed by Pseudomonas cepacia lipase

Biocatalytic Approaches to Optically Active &#946;-Blockers

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Biocatalytic Approaches to Optically Active β-Blockers