Esterification In Organic Solvents: Selection Of Hydrolases And Effects Of Reaction Conditions

Kawamoto, Takuo; Sonomoto, Kenji; Tanaka, Atsuo

doi:10.3109/10242428709040138

Cited by 72 publications

(25 citation statements)

References 19 publications

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“…Their special catalytic properties make them very attractive for industrial applications such as detergent industry, oleochemical industry, pulp and paper industry and resolution of chiral drugs [2,3]. While they can be used as a catalyst to cleavage ester bounds in the presence of water in reaction media, they catalyze formation of ester bound via esterification, inter-esterification and transesterification reactions in organic media [4]. It was also declared that esterases degraded natural materials and industrial pollutants such as cereal wastes, plastics and other toxic chemicals [5].…”

Section: Introductionmentioning

confidence: 99%

Purification and characterization of a pH and heat stable esterase from Geobacillus sp. TF17

Çolak

2013

Turk J Bioch

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Section: Introductionmentioning

confidence: 99%

Purification and characterization of a pH and heat stable esterase from Geobacillus sp. TF17

Çolak

2013

Turk J Bioch

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“…It is well known that water markedly affects the activity of enzymes in organic solvents (Kawamoto et al 1987;Zaks and Klibanov 1988). Furthermore, water, which is a product of the esterification, is presumed to accumulate in the reactor and inhibit the reaction during a long-term continuous reaction.…”

Section: Effect Of Water Content In Adsorbed Lipasementioning

confidence: 99%

Long-term continuous production of optically active 2-(4-chlorophenoxy)propanoic acid by yeast lipase in an organic solvent system

Fukui¹,

Kawamoto²,

Sonomoto³

et al. 1990

Appl Microbiol Biotechnol

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Long-term continuous optical resolution of 2-(4-chlorophenoxy)propanoic acid was carried out by stereoselective esterification with Celite-adsorbed lipase OF 360 from Candida cylindracea using n-tetradecanol as the second substrate in organic solvent systems. The water content of the Celite-adsorbed lipase affected productivity, 1.0 ~tl water-mg lipase -1 being optimal for preparation of the adsorbed lipase. Watersaturated carbon tetrachloride-isooctane (8:2, v/v) was found to be an excellent organic solvent for the continuous operation. The particle size of Celite had no effect on productivity. Under optimized conditions, the (R)-enantiomer of the acid was continuously esterified with high stereoselectivity in a packed-bed column reactor for 34 days. Furthermore, it was found that treatment of the reactor with acetone made it possible to restore productivity and extend the period of continuous operation for further 29 days.We have demonstrated bioconversion of various lipophilic compounds in organic solvent systems (Sonomoto and Tanaka 1988; Tanaka and Sonomoto 1990), such as the optical resolution of menthol (Koshiro et al. 1985) and 2-(4-chlorophenoxy)propanoic acid (Pan et al. 1990) by stereoselective esterification with lipase. In spite of much work on bioconversion in organic solvents, there have so far been only a few reports on continuous bioconversion (Macrae 1983;Nakanishi et al. 1985Nakanishi et al. , 1988Nakanishi et al. , 1990 and no study on a continuously operated system applying stereoselectivity of biocatalysts.This work deals with long-term continuous production of optically active 2-(4-chlorophenoxy)propanoic acid, the (R)-isomer of which is an important herbicide, by stereoselective esterification with n-tetradecanol by yeast lipase in organic solvents (Fig. 1), and with optimization of the reaction conditions.

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“…In organic media, they catalyse reactions such as esterification, inter-esterification and trans-esterification [3]. Esterases and lipases were first differentiated on the basis of their substrate specificity.…”

Section: Introductionmentioning

confidence: 99%

A thermoactive uropygial esterase from chicken: Purification, characterisation and synthesis of flavour esters

Fendri¹,

Louati²,

Sellami³

et al. 2012

International Journal of Biological Macromolecules

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Esterification In Organic Solvents: Selection Of Hydrolases And Effects Of Reaction Conditions

Cited by 72 publications

References 19 publications

Purification and characterization of a pH and heat stable esterase from Geobacillus sp. TF17

Purification and characterization of a pH and heat stable esterase from Geobacillus sp. TF17

Long-term continuous production of optically active 2-(4-chlorophenoxy)propanoic acid by yeast lipase in an organic solvent system

A thermoactive uropygial esterase from chicken: Purification, characterisation and synthesis of flavour esters

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