Lipase를 이용한 함불소화합물의 광학분할

손태일; Kitazume T

Journal of the Korean Industrial and Engineering Chemistry, Vol.5, No.1, 176-181, February, 1994

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Lipase를 이용한 함불소화합물의 광학분할

Biochemical Resolutions of Organic Florine Compounds Using Lipase

손태일, Kitazume T

초록

시판되고 있는 4종류의 Lipase(talpase, paratase M1000L, SP398, SP435)를 이용하여, 2-[1-(1-acetoxy-2,2, 2-trifluoroethyl)]-5-trimethylsilylfuran(1)을 속도론적 광학분할에 의해서 가수분해반응을 검토했다. 그 결과 Novo Nordish사의 SP435가 속도론적 광학분할능을 가진다는 것을 확인했으며, 본 실험에서는 광학순도 92.4% enantiomeric excess(ee)를 가지는 생성물 2-[1-(2, 2, 2-trifluoro-1-hydroxyethyl)]-5-trimethylsilyfuran(2)를 얻었다.

The hydrolysis of biochemical kinetic resolutions for 2-[1-(acetoxy-2, 2, 2-trifluoroethyl ]-5-trimethylsilylfuran(1) using kinds of Lifase(talpase, paratase, M1000L, SP398, SP435) was investigated. In the results SP435 of Novo Nordish comp any was confirmed to show the capacity of biochemical kinetic resolutions, and 2-(1-(2, 2, 2-trifluoro-1-hydroxyethyl)]-5-trimethylsilylfuran(2) to have the optical purity expressed as 92.4% enantiomeric excess(ee) was produced in this studies.

[References]

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[1] Kuroboshi M, Hiyama T, Abstracts of Papers, 15th Meeting of Fluorine Chemistry, Nagoya, Japan (1991)

[2] Kitazume T, Ishikawa N, J. Am. Chem. Soc., 109, 5186 (1985)

[3] Prakash GSK, Krishnamurti R, Olah G, J. Am. Chem. Soc., 111, 393 (1989)

[4] Krishnamurti R, Bellow DR, Prakash GSK, J. Org. Chem., 56, 984 (1991)

[5] Filler R, Kobayashi Y, "Biomedical Aspects of Fluorine Chemistry," Kodansha and Elsevier Biomedical, Tokyo (1982)

[6] Welch JT, Tetrahedron, 43, 3123 (1987)

[7] Seebach D, Angew. Chem.-Int. Edit., 29, 1320 (1990)

[8] Walsh C, Tetrahedron, 38, 871 (1982)

[9] Kitazume T, Ohnogi T, Ito K, J. Am. Chem. Soc., 112, 6608 (1990)

[10] Moden M, Shiromi M, Nakagawa K, Funada F, Awane K, Yamazaki T, Kitazume T, Jpn. J. Appl. Phys., 30, 1300 (1991)

[11] Glaudemans CPJ, Kovac P, Rusmussen K, Biochemistry, 23, 6732 (1984)

[12] Middleton WJ, J. Org. Chem., 40, 574 (1975)

[13] Hudlicky M, Org. React., 35, 513 (1988)

[14] Sondej SC, Katzenellenbogen JA, J. Org. Chem., 51, 3508 (1986)

[15] El-Langhdach A, Raouf R, Matheu MI, Barrena MI, Castillon S, J. Org. Chem., 56, 4556 (1991)

[16] Welch JT, Eswarakrishnan S, "Fluorine in Bioorganic Chemistry," John Wiley & Sons, New York (1991)

[17] Bravo P, Resnati G, Tetrahedron: Asymmetry, 1, 661 (1990)

[18] Vekemans JA, Dapperens CWM, Claessen R, Koten AMJ, Godefroi EF, J. Org. Chem., 55, 5336 (1990)

[19] Casiraghi G, Colombo L, J. Org. Chem., 56, 2135 (1991)

[20] Vigneron JP, Meric R, Tetrahedron, 40, 3521 (1984)

[21] Omura S, Sadakane N, Tanaka Y, Mayubara H, J. Antibiotics, 36, 927 (1983)

[22] Arcamore F, Franceshi G, Oremzi P, Cassinelle G, Barbieri W, Mondelli R, J. Am. Chem. Soc., 86, 5334 (1964)

[23] Hunt AH, Debono M, Merkei KE, Barnhart M, J. Org. Chem., 49, 635 (1984)

[24] Ojima I, Actual Chem., 171 (1987)

[25] Kitagawa O, Taguchi T, kobayashi Y, Tetrahedron Lett., 29, 1803 (1988)

[26] Yamazaki T, Yamamoto T, Kitazume T, J. Org. Chem., 54, 83 (1989)

[27] Chen CS, Fujimoto Y, Girdaukas G, Sih CJ, J. Am. Chem. Soc., 104, 7294 (1982)