Stereospecific hydrolysis 3-(4-methoxyphenyl)glycidic ester in supercritical carbon dioxide by immobilized lipase

Markku Rantakylä, Martti Alkio, Olli Aaltonen

Research output: Contribution to journalArticleScientificpeer-review

17 Citations (Scopus)

Abstract

In the hydrolysis of racemic 3-(4-methoxyphenyl)glycidic acid methyl ester by immobilized Mucor miehel lipase in supercritical CO2 the initial hydrolysis rate of the (2S,3R)-form was faster than the rate of the (2R,3S) -form. The stereoisomeric excess of the (2R,3S)-form reached 87 % at 53 % total conversion level. The water content of the reaction mixture and the initial concentration of the 3-(4-methoxyphenyl) glycidic acid methyl ester had no effect on isomeric purity. The reaction rate in supercritical CO2 was considerably faster than in toluene/water -mixture.
Original languageEnglish
Pages (from-to)1089-1094
Number of pages6
JournalBiotechnology Letters
Volume18
Issue number9
DOIs
Publication statusPublished - 1996
MoE publication typeA1 Journal article-refereed

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Lipases
Lipase
Carbon Dioxide
Hydrolysis
Carbon dioxide
Esters
Mucor
Acids
Water
Toluene
Water content
Reaction rates
glycidic acid

Cite this

Rantakylä, Markku ; Alkio, Martti ; Aaltonen, Olli. / Stereospecific hydrolysis 3-(4-methoxyphenyl)glycidic ester in supercritical carbon dioxide by immobilized lipase. In: Biotechnology Letters. 1996 ; Vol. 18, No. 9. pp. 1089-1094.
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abstract = "In the hydrolysis of racemic 3-(4-methoxyphenyl)glycidic acid methyl ester by immobilized Mucor miehel lipase in supercritical CO2 the initial hydrolysis rate of the (2S,3R)-form was faster than the rate of the (2R,3S) -form. The stereoisomeric excess of the (2R,3S)-form reached 87 {\%} at 53 {\%} total conversion level. The water content of the reaction mixture and the initial concentration of the 3-(4-methoxyphenyl) glycidic acid methyl ester had no effect on isomeric purity. The reaction rate in supercritical CO2 was considerably faster than in toluene/water -mixture.",
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Stereospecific hydrolysis 3-(4-methoxyphenyl)glycidic ester in supercritical carbon dioxide by immobilized lipase. / Rantakylä, Markku; Alkio, Martti; Aaltonen, Olli.

In: Biotechnology Letters, Vol. 18, No. 9, 1996, p. 1089-1094.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Stereospecific hydrolysis 3-(4-methoxyphenyl)glycidic ester in supercritical carbon dioxide by immobilized lipase

AU - Rantakylä, Markku

AU - Alkio, Martti

AU - Aaltonen, Olli

N1 - Project code: KET0401

PY - 1996

Y1 - 1996

N2 - In the hydrolysis of racemic 3-(4-methoxyphenyl)glycidic acid methyl ester by immobilized Mucor miehel lipase in supercritical CO2 the initial hydrolysis rate of the (2S,3R)-form was faster than the rate of the (2R,3S) -form. The stereoisomeric excess of the (2R,3S)-form reached 87 % at 53 % total conversion level. The water content of the reaction mixture and the initial concentration of the 3-(4-methoxyphenyl) glycidic acid methyl ester had no effect on isomeric purity. The reaction rate in supercritical CO2 was considerably faster than in toluene/water -mixture.

AB - In the hydrolysis of racemic 3-(4-methoxyphenyl)glycidic acid methyl ester by immobilized Mucor miehel lipase in supercritical CO2 the initial hydrolysis rate of the (2S,3R)-form was faster than the rate of the (2R,3S) -form. The stereoisomeric excess of the (2R,3S)-form reached 87 % at 53 % total conversion level. The water content of the reaction mixture and the initial concentration of the 3-(4-methoxyphenyl) glycidic acid methyl ester had no effect on isomeric purity. The reaction rate in supercritical CO2 was considerably faster than in toluene/water -mixture.

U2 - 10.1007/BF00129737

DO - 10.1007/BF00129737

M3 - Article

VL - 18

SP - 1089

EP - 1094

JO - Biotechnology Letters

JF - Biotechnology Letters

SN - 0141-5492

IS - 9

ER -