Ester synthesis by the lipase from Pseudomonas fragi 22.39 B.

Nishio, Takeshi; Chikano, Takahide; Kamimura, Minoru

doi:10.1271/bbb1961.52.1203

Cited by 30 publications

(4 citation statements)

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“…In the supercritical fluid system, however, the distribution of water is uniform, and that water contributes to mass-transfer resistance by forming a film around the enzyme. Others , who have investigated the synthesis of esters in hexane have also observed that the water content of the system does not influence the conversion. Nishio et al observed that the synthesis of n -butyl oleate was not affected very much by the amount of water in the mixture.…”

Section: Resultsmentioning

confidence: 99%

“…Others , who have investigated the synthesis of esters in hexane have also observed that the water content of the system does not influence the conversion. Nishio et al observed that the synthesis of n -butyl oleate was not affected very much by the amount of water in the mixture. Zaks and Klibanov 13 showed that the water content does not influence the activity of M. meihei lipase.…”

Section: Resultsmentioning

confidence: 99%

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Enzymatic Synthesis of Flavors in Supercritical Carbon Dioxide

Srivastava

Modak

Madras

2002

Ind. Eng. Chem. Res.

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Commercially important flavor esters of isoamyl alcohol, catalyzed by crude hog pancreas lipase (HPL), were synthesized under solvent-free conditions and in supercritical carbon dioxide. The esters synthesized were isoamyl acetate, isoamyl propionate, isoamyl butyrate, and isoamyl octanoate. Very low yields (3-4%) of isoamyl acetate were obtained, but high yields for the other three esters were obtained under both supercritical and solvent-free conditions. The yields of esters of the even-carbon acids, isoamyl acetate, butyrate, and octanoate, increased with increasing chain length, whereas the yield of isoamyl propionate was higher than that of isoamyl butyrate. The optimum temperature of the reaction was higher under supercritical conditions (45 °C) than under solvent-free conditions (35-40 °C). The effects of other parameters such as alcohol concentration, water concentration, and enzyme loading were investigated. An increase in the water concentration decreased the conversion significantly in supercritical carbon dioxide but not under solvent-free conditions. The optimum ratio of alcohol to acid was dependent on the extent of inhibition by the acid. Although providing a higher apparent yield by being run in a highly concentrated medium, the overall conversion under solvent-free conditions was lower than that under supercritical conditions for similar enzyme concentrations, indicating that the synthesis of esters in supercritical carbon dioxide might be a viable option.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Enzymatic Synthesis of Flavors in Supercritical Carbon Dioxide

Srivastava

Modak

Madras

2002

Ind. Eng. Chem. Res.

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“…However, lipases from pseudomonads can also synthesise short-, medium-and long-chain esters via esterification in both organic and aqueous media (Nishio, Chikano, & Kamimura, 1988;Tan & Apenten, 1995;Tweddell, Kermasha, Combes, & Marty, 1997;Wehtje & Adlercreutz, 1997a, b). In addition to esterases and lipases, the existence of other ester-synthesising enzymes such as alcohol acyltransferases in pseudomonads remains to be explored.…”

Section: Ester Biosynthesis By Dairy Pseudomonadsmentioning

confidence: 99%

Esters and their biosynthesis in fermented dairy products: a review

Liu

Holland

Crow

2004

International Dairy Journal

338

269

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“…The ester formation catalysed by lipase has been shown to be influenced by the alcohol moiety..4, niger, G. candidum, Penicillium cyclopium and Rhizopus delemar (Okumura et al 1979), Pseudomonasfragi (Nishio et al 1988) and Rhizomucor miehei (Gatfield 1984) are able to synthesize esters of various primary alcohols, but they are not able to esterify the tertiary alcohols at all. A m o n g these lipases, only those of G. candidum, P. fragi and R. miehei can use various secondary alcohols as substrates, although the activities are.…”

Section: Effect O F Alcohol Moietymentioning

confidence: 99%

Use of lipases in the resolution of racemic ibuprofen

Mustranta

1992

Appl Microbiol Biotechnol

147

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Resolution of (R,S)-ibuprofen enantiomers by esterification in different organic solvents was studied using Candida cylindracea lipase. This enzyme preparation had high enantiospecificity for S(+)-ibuprofen in the esterification reaction of a racemic ibuprofen with primary alcohols. The esterification yields of secondary alcohols were much lower than those of primary alcohols. Esterification with tertiary alcohols was not observed. The synthesis of esters was profoundly affected by the amount of water in the reaction mixture. C. cylindracea lipase was active only in very hydrophobic solvents. The esterification activity of the lipase was reduced significantly by addition of water. The R- and S-enantiomers of ibuprofen were determined without derivatization by HPLC using a chiral column.

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Ester synthesis by the lipase from Pseudomonas fragi 22.39 B.

Cited by 30 publications

References 1 publication

Enzymatic Synthesis of Flavors in Supercritical Carbon Dioxide

Enzymatic Synthesis of Flavors in Supercritical Carbon Dioxide

Esters and their biosynthesis in fermented dairy products: a review

Use of lipases in the resolution of racemic ibuprofen

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