Enancjoselektywna enzymatyczna desymetryzacja katalizowana lipazami. Część 1, Związki prochiralne

Kołodziejska, R.; Karczmarska-Wódzka, A.; Tafelska-Kaczmarek, A.; Studzińska, R.; Dramiński, M.

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Enancjoselektywna enzymatyczna desymetryzacja katalizowana lipazami. Część 1, Związki prochiralne

Autorzy

Kołodziejska R. , Karczmarska-Wódzka A. , Tafelska-Kaczmarek A. , Studzińska R. , Dramiński M.

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Warianty tytułu

Enantioselectve enzymatic desymmetrization catalyzed in the presence of lipase. Part 1, Prochiral compounds

Języki publikacji

Abstrakty

In the enzymatic asymmetric synthesis, the enzyme allows the desymmetrization of achiral compounds resulting in chiral compounds of high optical purity. Therefore, this type of biotransformation is known as enantioselective enzymatic desymmetrization (EED) [1–11]. This method is related to the generation of an asymmetry (loss of symmetry elements) in prochiral molecules (most often an sp3 or sp2 hybridized carbon atom), in meso synthones, and centrosymmetric compounds. An achiral center of the tetrahedral system is defined as a prochiral one if it becomes chiral as a result of one of the two substituents replacement which, when separated from the particles, are indistinguishable (Scheme 1, 2) [1–4, 9, 12]. Asymmetric synthesis is enantioselective when one of the enantiotopic groups or faces of an optically inactive compound is biotransformed faster than the other (Scheme 3–5) [1, 10, 11, 13–15]. Lipases are enzymes of highest importance in stereoselective organic synthesis, mainly due to their exceptionally broad substrate tolerance, stability, activity in unphysiological systems, and relatively low price [9, 14]. The mechanism of enzymatic hydrolysis catalysed by hydrolases is similar to that observed in the chemical hydrolysis with the use of base. The selectivity of enzymatic catalysis depends on the substrate orientation in the enzyme active site (Scheme 6, 7) [25–29]. Lipases were successfully used for the desymmetrization of different prochiral diesters, alcohols and amines. Most lipases preferentially convert the same prochiral groups in the above mentioned types of reaction. This allows the preparation of the both enantiomers of the product in high chemical and optical yield (Scheme 9–13) [9, 13, 32–56].

Słowa kluczowe

związki prochiralne desymetryzacja transestryfikacja hydroliza lipazy

prochiral compounds desymmetrization transesterification hydrolysis lipase

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2013

Tom

[Z] 67, 7-8

Strony

751--772

Opis fizyczny

Bibliogr. 56 poz., schem.

Twórcy

autor

Kołodziejska R.

Katedra i Zakład Chemii Ogólnej, Collegium Medicum w Bydgoszczy UMK Toruń ul. Dębowa 3, 85-626 Bydgoszcz

autor

Karczmarska-Wódzka A.

Katedra i Zakład Chemii Ogólnej, Collegium Medicum w Bydgoszczy UMK Toruń ul. Dębowa 3, 85-626 Bydgoszcz

autor

Tafelska-Kaczmarek A.

Katedra Chemii Organicznej, UMK Toruń ul. Gagarina 7, 87-100 Toruń

autor

Studzińska R.

Katedra i Zakład Chemii Ogólnej, Collegium Medicum w Bydgoszczy UMK Toruń ul. Dębowa 3, 85-626 Bydgoszcz

autor

Dramiński M.

Katedra i Zakład Chemii Ogólnej, Collegium Medicum w Bydgoszczy UMK Toruń ul. Dębowa 3, 85-626 Bydgoszcz

Bibliografia

[1] J. Gawroski, K. Gawroska, Stereochemia w syntezie organicznej, PWN, Warszawa, 1988.
[2] I .Z. Siemion, Biostereochemia, PWN, Warszawa, 1985.
[3] F .A. Carey, R.J. Sundberg, Advanced Organic Chemistry, Springer: New York, 2007.
[4] C h.-S. Chen, Y. Fujimoto, G. Girdaukas, Ch. J. Sih, J. Am. Chem. Soc., 1982, 104, 7294.
[5] V . Gotor-Fernandez, E. Busto, V. Gotor, Adv. Synth. Catal., 2006, 384, 797.
[6] K. Frings, M. Koch, W. Hartmeier, Enzyme and Microbial Technology, 1999, 25, 303.
[7] M.-J. Kim, Y. Ann, J. Park, Bull. Korean Chem. Soc., 2005, 26, 515.
[8] B .A. Persson, A.L.E. Larsson, M.L. Ray, J.-E. Backvall, J. Am. Chem. Soc., 1999, 121, 1645.
[9] E . Garcia-Urdiales, I. Alfonso, V. Gotor, Chem. Rev., 2005, 105, 313.
[10] Y .-F. Wang, Ch.-S. Chen, G. Girdaukas, Ch. J. Sih, J. Am. Chem. Soc., 1984, 106, 3695.
[11] C h. J. Sih, W.-R. Shieh, Ch.-S. Chen, S.-H. Wu, G. Girdaukas, 1986, International Synposium on Bioorganic Chemistry, 239.
[12] R . Koodziejska, M. Gorecki, J. Frelek, M. Dramiski, Tetrahedron: Asymmetry, 2012, 23, 623.
[13] V . Gotor, I. Alfonso, E. Garcia-Urdiales, Asymmetric organic synthesis with enzymes, Willey-VCH ., Weinheim, 2008.
[14] K. Faber, Biotransformations in organic chemistry, Springer, Berlin, 1992.
[15] C h.-S. Chen, Y. Fujimoto, Ch. J. Sih, J. Am. Chem. Soc., 1981, 103, 3580.
[16] H .-H. Otto, T. Schirmeister, Chem. Rev., 1997, 97, 133.
[17] M.J. Harrison, N.A. Burton, I.H. Hillier, I.R. Gould, Chem. Commun., 1996, 2769.
[18] A . Fersht, Enzyme Structure and Mechanism, Wyd. 2, Freeman, New York, 1985.
[19] J. Uppenberg, N. Ohrner, M. Norin, K. Hult, G.J. Kleywegt, F. Spener, R.D. Schimd, D. Schoburg, J. Mol. Biol., 1996, 259, 704.
[20] A .M. Brzozowski, U. Derewenda, Z.S. Derewenda, G.G. Dodson, D.M. Lawson, J.P. Turkenburg, F. Bjorkling, B. Huge-Jensen, S. Patkar, L. Thim, Nature, 1991, 351, 491.
[21] U . Derewenda, A.M. Brzozowski, D.M. Lawson, Z.S. Derewenda, Biochemistry, 1992, 31, 1532.
[22] C . Martinez, A. Nicolas, H. Van Tilbeurgh, M. P. Egloff, C. Cudrey, R. Verger, C. Cambillau, Biochemistry, 1994, 15, 29.
[23] K.E. Jaeger, S. Ransac, B.W. Dijkstra, C. Colson, M. Van Heuvel, O. Misset, FEMS Microbiol. Rev., 1994, 15, 29.
[24] M. Martinelle, M. Holmquist, K. Hult, Biochim. Biophys. Acta, 1995, 1258, 272.
[25] J. Orrenius, F. Haffner, D. Rotticci, N. Ohrner, T. Norin, K. Hult, Biocatal. Biotransform., 1998, 16, 1.
[26] J. Uppenberg, N. Ohrner, M. Norin, K. Hult, G.J. Kleywegt, S. Patkar, V. Waagen, T. Anthonsen, T.A. Jones, Biochemistry, 1995, 34, 16838.
[27] J. Ottosson, J. C. Rotticci-Mulder, D. Rotticci, K. Hult, Protein Science, 2001, 10, 1769.
[28] K. Faber, G. Ottolina, S. Riva, Biocatalysis and Biotransformation, 1993, 8, 91.
[29] M . Holmquist, F. Haffner, T. Norin, K. Hult, Protein Science, 1996, 5, 83.
[30] R . Chenevert, N. Pelchat, P. Morin, Tetrahedron: Asymmetry, 2009, 20, 1191.
[31] I . Izquierdo, M.T. Plaza, M. Rodriguez, J. Tamayo, Tetrahedron: Asymmetry, 1999, 10, 449.
[32] I .M. Fellows, D.E. Kaelin, S.F. Martin, J. Am. Chem. Soc., 2000, 122, 10781.
[33] D .B. Kastrinsky, D.L. Boger, J. Org. Chem., 2004, 69, 2284.
[34] B . Morgan, D.R. Dodds, A. Zaks, D.R. Andrews, R. Klesse, J. Org. Chem., 1997, 62, 7736.
[35] K. Takabe, N. Mase, H. Hashimoto, A.Tsuchiya, T. Ohbayasi, H. Yoda, Bioorg. Med. Chem. Lett., 2003, 13, 1967.
[36] T . Yokomatsu, K. Takada, A. Yasumoto, Y. Yuasa, S. Shibuya, Heterocycles, 2002, 5.
[37] C h.M. Sapu, J.-E. Backvall, J. Deska, Angew. Chem. Int. Ed., 2011, 50, 9731.
[38] C h.M. Sapu, J. Deska, Org. Biomol. Chem., 2013, 11, 1376.
[39] C . Neri, J.M.J. Williams, Adv. Synth. Catal., 2003, 345, 835.
[40] J.Y. Choi, R.F. Borch, Org. Lett., 2007, 18, 215.
[41] T . Tsuji, Y. Iio, T. Takemoto, T. Nishi, Tetrahedron: Asymmetry, 2005, 16, 3139.
[42] K. Takabe, Y. Iida, H. Hiyoshi, M. Ono, Y. Hirose, Y. Fukui, H. Yoda, N. Mase, Tetrahedron: Asymmetry, 2000, 11, 4825.
[43] M. Kirihara, M. Kawasaki, T. Takuwa, H. Kakuda, T. Wakikawa, Y. Takeuchi, K.L. Kirk, Tetrahedron: Asymmetry, 2003, 14, 1753.
[44] N . Rios-Lombardia, E. Busto, E. Garcia-Urdiales, V. Gotor-Fernandez, V. Gotor, J. Org. Chem., 2009, 74, 2571.
[45] V . Bdai, L. Novak, L. Poppe, Synlett., 1999, 759.
[46] R . Chenevert, G. Courchesne, N. Pelchat, Bioorganic & Medical Chemistry, 2006, 14, 5389.
[47] K. Shimada, Y. Kauragi, T. Fukuyama, J. Am. Chem. Soc., 2003, 125, 4048.
[48] R . Chenevert, M. Simard, J. Bergeron, M. Dasser, Tetrahedron: Asymmetry, 2004, 15, 1889.
[49] S . Akai, T. Tsujino, E. Akiyama, K. Tanimoto, T. Naka, Y. Kita, J. Org. Chem., 2004, 69, 2478.
[50] A . Soriente, G. Laudisio, M. Giordano, G. Sodano, Tetraedron: Asymmetry, 1995, 6, 859.
[51] N . Rios-Lombardia, V. Gotor-Fernandez, V. Gotor, J. Org. Chem., 2011, 76, 811.
[52] M.J. Homann, R. Vail, B. Morgan, V. Sabesan, C. Levy, D.R. Dodds, A. Zaks, Adv. Synth. Catal., 2001, 343, 744.
[53] J.-H. Jung, D.-H. Yoon, P. Kang, W.K. Lee, H. Eum, H.-J. Ha, Org. Biomol. Chem., 2013, 11, 3635.
[54] M. Lpez-Garcia, I. Alfonso, V. Gotor, Tetrahedron: Asymmetry, 2003, 14, 603.
[55] R . Ostaszewski, D.E. Portlock, A. Fryszkowska, K. Jeziorska, Pure Appl. Chem., 2003, 75, 413.
[56] A . Fryszkowska, M. Komar, D. Koszelewski, R. Ostaszewski, Tetrahedron: Asymmetry, 2005, 16, 2475.

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Bibliografia

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