Enzyme-catalyzed asymmetric acylation and hydrolysis of cis-2,5-disubstituted tetrahydrofuran derivatives: Contribution to development of models for reactions catalyzed by porcine liver esterase and porcine pancreatic lipase

Koichiro Naemura; Ritsuko Fukuda; Nobuo Takahashi; Masayoshi Konishi; Yoshiki Hirose; Tobe Yoshito

doi:10.1016/S0957-4166(00)80131-7

Enzyme-catalyzed asymmetric acylation and hydrolysis of cis-2,5-disubstituted tetrahydrofuran derivatives: Contribution to development of models for reactions catalyzed by porcine liver esterase and porcine pancreatic lipase

Koichiro Naemura^*, Ritsuko Fukuda, Nobuo Takahashi, Masayoshi Konishi, Yoshiki Hirose, Tobe Yoshito

^*Corresponding author for this work

Department of Applied Chemistry

Research output: Contribution to journal › Article

30 Scopus citations

Abstract

Pig liver esterase, lipase from porcine pancreas, lipase from Pseudomonas sp. (lipase YS), and lipase from Candida cylindracea catalyzed hydrolyses of the cis-diacetate 1 and the trans-diacetate (±)-4 to give the cis-monoacetate 3 and the trans-monoacetate 6 in optically active forms, respectively. Lipase YS-catalyzed acylations of the cis-diol 2 and the trans-diol (±)-5 with an acylating agent in cyclohexane yielded (-)-3 and (-)-6, respectively. The group adjacent to the R stereogenic center preferentially reacted in lipase YS-catalyzed hydrolyses of 1 and (±)-4 and acylations of 2 and (±)-5, and the enantioselectivities are rationalized by our rule recently proposed for lipase YS.

Original language	English
Pages (from-to)	911-918
Number of pages	8
Journal	Tetrahedron: Asymmetry
Volume	4
Issue number	5
DOIs	https://doi.org/10.1016/S0957-4166(00)80131-7
State	Published - 1 Jan 1993

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Naemura, K., Fukuda, R., Takahashi, N., Konishi, M., Hirose, Y., & Yoshito, T. (1993). Enzyme-catalyzed asymmetric acylation and hydrolysis of cis-2,5-disubstituted tetrahydrofuran derivatives: Contribution to development of models for reactions catalyzed by porcine liver esterase and porcine pancreatic lipase. Tetrahedron: Asymmetry, 4(5), 911-918. https://doi.org/10.1016/S0957-4166(00)80131-7

Naemura, Koichiro ; Fukuda, Ritsuko ; Takahashi, Nobuo ; Konishi, Masayoshi ; Hirose, Yoshiki ; Yoshito, Tobe. / Enzyme-catalyzed asymmetric acylation and hydrolysis of cis-2,5-disubstituted tetrahydrofuran derivatives : Contribution to development of models for reactions catalyzed by porcine liver esterase and porcine pancreatic lipase. In: Tetrahedron: Asymmetry. 1993 ; Vol. 4, No. 5. pp. 911-918.

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abstract = "Pig liver esterase, lipase from porcine pancreas, lipase from Pseudomonas sp. (lipase YS), and lipase from Candida cylindracea catalyzed hydrolyses of the cis-diacetate 1 and the trans-diacetate (±)-4 to give the cis-monoacetate 3 and the trans-monoacetate 6 in optically active forms, respectively. Lipase YS-catalyzed acylations of the cis-diol 2 and the trans-diol (±)-5 with an acylating agent in cyclohexane yielded (-)-3 and (-)-6, respectively. The group adjacent to the R stereogenic center preferentially reacted in lipase YS-catalyzed hydrolyses of 1 and (±)-4 and acylations of 2 and (±)-5, and the enantioselectivities are rationalized by our rule recently proposed for lipase YS.",

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Naemura, K, Fukuda, R, Takahashi, N, Konishi, M, Hirose, Y & Yoshito, T 1993, 'Enzyme-catalyzed asymmetric acylation and hydrolysis of cis-2,5-disubstituted tetrahydrofuran derivatives: Contribution to development of models for reactions catalyzed by porcine liver esterase and porcine pancreatic lipase', Tetrahedron: Asymmetry, vol. 4, no. 5, pp. 911-918. https://doi.org/10.1016/S0957-4166(00)80131-7

Enzyme-catalyzed asymmetric acylation and hydrolysis of cis-2,5-disubstituted tetrahydrofuran derivatives : Contribution to development of models for reactions catalyzed by porcine liver esterase and porcine pancreatic lipase. / Naemura, Koichiro; Fukuda, Ritsuko; Takahashi, Nobuo; Konishi, Masayoshi; Hirose, Yoshiki; Yoshito, Tobe.

In: Tetrahedron: Asymmetry, Vol. 4, No. 5, 01.01.1993, p. 911-918.

Research output: Contribution to journal › Article

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T1 - Enzyme-catalyzed asymmetric acylation and hydrolysis of cis-2,5-disubstituted tetrahydrofuran derivatives

T2 - Contribution to development of models for reactions catalyzed by porcine liver esterase and porcine pancreatic lipase

AU - Naemura, Koichiro

AU - Fukuda, Ritsuko

AU - Takahashi, Nobuo

AU - Konishi, Masayoshi

AU - Hirose, Yoshiki

AU - Yoshito, Tobe

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AB - Pig liver esterase, lipase from porcine pancreas, lipase from Pseudomonas sp. (lipase YS), and lipase from Candida cylindracea catalyzed hydrolyses of the cis-diacetate 1 and the trans-diacetate (±)-4 to give the cis-monoacetate 3 and the trans-monoacetate 6 in optically active forms, respectively. Lipase YS-catalyzed acylations of the cis-diol 2 and the trans-diol (±)-5 with an acylating agent in cyclohexane yielded (-)-3 and (-)-6, respectively. The group adjacent to the R stereogenic center preferentially reacted in lipase YS-catalyzed hydrolyses of 1 and (±)-4 and acylations of 2 and (±)-5, and the enantioselectivities are rationalized by our rule recently proposed for lipase YS.

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Naemura K, Fukuda R, Takahashi N, Konishi M, Hirose Y, Yoshito T. Enzyme-catalyzed asymmetric acylation and hydrolysis of cis-2,5-disubstituted tetrahydrofuran derivatives: Contribution to development of models for reactions catalyzed by porcine liver esterase and porcine pancreatic lipase. Tetrahedron: Asymmetry. 1993 Jan 1;4(5):911-918. https://doi.org/10.1016/S0957-4166(00)80131-7