Abstract
The currently known methods of enzymatic β-lactam synthesis, as well as the enzymes and heterogeneous biocatalysts used for this purpose, are presented, and the published reports on advances in the field of enzymatic synthesis of selected antibiotics belonging to the groups of penicillin acids and cephalosporin acids are summarized in the present review. The key conditions and parameters of biocatalytic processes, such as the biocatalyst form, concentration of the precursor compounds, solvent type, pH, temperature, etc. are analyzed and compared, and guidelines for further optimization of β-lactam synthesis are given. The present review may be of use for a wide range of readers, as well as to enzymology and biotechnology experts.
Similar content being viewed by others
References
Van Krimpen, P.C., Van Bennekom, W.P., and Bult, A., Pharm. Weekbl. Sci., 1987, vol. 9, no. 1, pp. 1–23.
Elks, J., Drugs, 1987, vol. 34, suppl. 2, pp. 240–246.
Nys, P.S., Kurochkina, V.B., Sklyarenko, A.V., and Egorov, M.A., Antibiot. Khimioter., 2000, vol. 45, no. 11, pp. 36–42.
Kurochkina, V.B. and Nys, P.S., Antibiot. Khimioter., 2002, vol. 47, no. 2, pp. 29–37.
Kurochkina, V.B. and Nys, P.S., Khim-Farm. Zh., 2003, vol. 37, no. 126, pp. 33–40.
Kurochkina, V.B., Sklyarenko, AV., Satarova, J.E., and Yarotsky, S.V., Bioprocess Biosyst. Eng., 2011, vol. 34, no. 9, pp. 1103–1117.
Elander, R.P., Appl. Microbiol. Biotechnol., 2003, vol. 61, nos 5–6, pp. 385–392.
Schmidt, F-R., in The Mycota. X Industrial Applications, 2nd. ed., Esser, K. and Hofrichter, M., Eds., Berlin, Heidelberg: Springer-Verlag, vol. 5, pp. 101–121.
Volpato, G., Rodrigues, R.C., and Fernandez-Lafuente, R., Curr. Med. Chem., 2010, vol. 17, no. 32, pp. 3855–3873.
Kurochkina, V.B. and Sklyarenko, A.V., Antibiot. Khimioter., 2005, vol. 50, no. 5–6, pp. 39–58.
Sklyarenko, A.V., Kurochkina, V.B., and Egorov, A.M., in New Research on Biotechnology in Biology and Medicine, Egorov, A.M. and Zaikov, G., Eds., Nova Science Publishers, 2006, ch. 8, pp. 73–86.
Synthesis of beta-Lactam Antibiotics: Chemistry, Biocatalysis and Process Integration, Bruggink, A., Ed., Dordrecht: Kluver Academic Publishers, 2001.
Deaguero, A.L., Blum, J.K., and Bommarius, A.S., in Encyclopedia of Industrial Biotechnology: Bioprocess, Bioseparation, and Cell Technology, Flickinger, M.C., Ed., John Wiley and Sons, 2010, pp. 535–567.
Barber, M.S., Giesecke, U., Reichert, A., and Minas, W., Adv. Biochem. Eng. Biotechnol., 2004, vol. 88, pp. 179–215.
Illanes, A., Cauerhff, A., Wilson, L., and Castro, G.R., Bioresour. Technol., 2012, vol. 115, pp. 48–57.
Hernández-Jústiz, O., Terreni, M., Pagani, G., Garcìa, J., Guisan, J., and Fernandez-Lafuente, R., Enzyme Microb. Technol., 1999, vol. 25, nos. 3–5, pp. 336–343.
WO Patent no. 2004039997, 2004.
Kostadinov, M., Nikolov, A., Tsoneva, N., and Petkov, N., Appl. Biochem. Biotechnol., 1992, vol. 33, no. 3, pp. 177–182.
Bruggink, A., Roos, E.C., and de Vroom, E., Org. Process Res. Dev., 1998, vol. 2, no. 2, pp. 128–133.
Hewitt, L., Kasche, V., Lummer, K., Lewis, R.J., Murshudov, G.N., Verma, C.S., Dodson, G.G., and Wilson, K.S., J. Mol. Biol., 2000, vol. 302, no. 4, pp. 887–898.
Alkema, W.B., Hensgens, C.M., Kroezinga, E.H., de Vries, E., Floris, R., van der Laan, J.M., Dijkstra, B.W., and Janssen, D.B., Protein Eng., 2000, vol. 13, no. 12, pp. 857–863.
Srirangan, K., Orr, V., Akawi, L., Westbrook, A., Moo-Young, M., and Chou, C.P., Biotechnol. Adv., 2013, vol. 31, no. 8, pp. 1319–1332.
Grulich, M., Stěpanek, V., and Kyslik, P., Biotechnol. Adv., 2013, vol. 31, no. 8, pp. 1458–1472.
Chandel, A.K., Rao, L.V., Narasu, M.L., and Singh, O.V., Enzyme Microb. Technol., 2008, vol. 42, no. 3, pp. 199–207.
Senerovic, L., Stankovic, N., Spizzo, P., Basso, A., Gardossi, L., Vasiljevic, B., Ljubijankic, G., Tisminetzky, S., and Degrassi, G., Biotechnol. Bioeng., 2006, vol. 93, no. 2, pp. 344–354.
Panin, N., Sultanov, D., Kirilin, E., Shcherbakova, T., Kudravtsev, P., and Svedas, V., FEBS J., 2013, vol. 280, no. 1, p. 614.
Orr, V., Scharer, J., Moo-Young, M., Honeyman, C.H., Fenner, D., Crossley, L., Suen, S.Y., and Chou, C.P., J. Biotechnol., 2012, vol. 161, no. 1, pp. 19–26.
Palomo, J., Curr. Org. Synth., 2009, vol. 6, no. 1, pp. 1–14.
Grazú V., López-Gallego F., Montes T., Abian O., Gonzá-lez R., Hermoso J.A., García J.L, Mateo C., Guisán J.M., Process Biochem., 2010, vol. 45, pp. 390–398.
Mateo, C., Abian, O., Fernandez-Lafuente, R., and Guisan, J.M., Enzyme Microb. Technol., 2000, vol. 26, no. 3, pp. 509–515.
Kallenberg, A.I., van Rantwijk, F., and Sheldon, R.A., Adv. Synth. Catal., 2005, vol. 347, nos. 7–8, pp. 905–926.
Mateo, C., Abian, O., Fernández-Lorente, G., Pedroche, J., Fernandez-Lafuente, R., Guisan, J.M., Tam, A., and Daminati, M., Biotechnol. Prog., vol. 18, no. 3, pp. 629–636.
Fernandez-Lafuente, R., Rosell, C.M., Caanan-Haden, L., Rodes, L., and Guisan, J.M., Enzyme Microb. Technol., 1999, vol. 24, nos. 1–2, pp. 96–103.
Abian, O., Ferna, G., and Guisa, M., Biotechnol. Prog., 2004, vol. 20, no. 1, pp. 117–121.
Estruch, I., Tagliani, A.R., Guisán, J.M., Fernandez-Lafuente, R., Alcantara, A.R., Toma, L., and Terreni, M., Enzyme Microb. Technol., 2008, vol. 42, no. 2, pp. 121–129.
Wilson, L., Illanes, A., Romero, O., and Vergara, J.M.C., Enzyme Microb. Technol., 2008, vol. 43, no. 6, pp. 442–447.
Xu, Y., Rosenkranz, S., Weng, C-L., Scharer, J.M., Moo-Young, M., and Chou, C.P., Appl. Microbiol. Biotechnol., 2006, vol. 72, no. 3, pp. 529–536.
Narayanan, N., Hsieh, M-Y., Xu, Y., and Chou, C.P., Biotechnol. Prog., 2005, vol. 22, no. 3, pp. 617–625.
Narayanan, N., Xu, Y., and Chou, C.P., Biotechnol. Prog., 2006, vol. 22, no. 6, pp. 1518–1523.
Vélez, A.M., Silva, A.J., Luperni Horta, A.C., Sargo, C.R., Campani, G., Gonçalves Silva, G., de Lima Camargo Giordano, R., and Zangirolami, T.C., BMC Biotechnol., 2014, vol. 14, no. 1, p. 6.
Ignatova, Z., Enfors, S., Hobbie, M., Taruttis, S., Vogt, C., and Kasche, V., Enzyme Microb. Technol., 2000, vol. 26, nos. 2–4, pp. 165–170.
Scherrer, S., Robas, N., Zouheiry, H., Branlant, G., and Branlant, C., Appl. Microbiol. Biotechnol., 1994, vol. 42, no. 1, pp. 85–91.
Sriubolmas, N., Panbangred, W., Sriurairatana, S., and Meevootisom, V., Appl. Microbiol. Biotechnol., 1997, vol. 47, no. 4, pp. 373–378.
Pan, K-L., Hsiao, H-C., Weng, C-L., Wu, M-S., and Chou, C.P., J. Bacteriol., 2003, vol. 185, no. 10, pp. 3020–3030.
RF Patent no. 2420581, 2011.
Patent of China no. CN 102296057, 2011.
Mardanov, A.V., Eldarov, M.A., Sklyarenko, A.V., Dumina, M.V., Beletsky, A.V., Yarotsky, S.V., and Ravin, N.V., Genome Announc., 2014, vol. 2, no. 6, p. e01222-14.
El’darov, M.A., Sklyarenko, A.V., Mardanov, A.V., Beletskii, A.V., Dumina, M.V., Medvedeva, N.V., Satarova, D.E., Ravin, N.V., and Yarotskii, S.V., Prikl. Biokhim. Mikrobiol., 2015, vol. 51, no. 5, pp. 465–471.
Kurochkina, V.B. and Nys, P.S., Biocatal. Biotransform., 2002, vol. 20, no. 1, pp. 35–41.
Margolin, A.L., Shvyadas, V.K., Nys, P.S., Kol’tsova, E.V., Savitskaya, E.M., and Berezin, I.V., Antibiotiki, 1978, vol. 23, no. 2, pp. 114–118.
Margolin, A.L., Svedas, V.K., and Berezin, I.V., Biochim. Biophys. Acta, 1980, vol. 616, no. 2, pp. 283–289.
Švedas, V.K., Margolin, A.L., and Berezin, I.V., Enzyme Microb. Technol., 1980, vol. 2, no. 2, pp. 138–144.
Fernandez-Lafuente, R., Rosell, C.M., and Guisán, J.M., Enzyme Microb. Technol., 1991, vol. 13, no. 11, pp. 898–905.
Fernandez-Lafuente, R., Alvaro, G., Blanco, R.M., and Guisan, J.M., Appl. Biochem. Biotechnol., 1991, vol. 27, no. 3, pp. 277–290.
Fernandez-Lafuente, R., Rosell, C.M., and Guisan, J.M., Biotechnol. Appl. Biochem., 1996, vol. 24, no. 2, pp. 139–143.
Nys, P.S. and Kurochkina, V.B., Appl. Biochem. Biotechnol., 2000, vol. 88, nos. 1–3, pp. 221–230.
Fernandez-Lafuente, R., Rosell, C.M., Piatkowska, B., and Guisan, J.M., Enzyme Microb. Technol., 1996, vol. 19, no. 1, pp. 9–14.
Kim, M.G. and Lee, S.B., J. Mol. Catal., 1996, vol. 1, nos. 3–6, pp. 201–211.
Rosell, C.M., Terreni, M., Fernandez-Lafuente, R., and Guisan, J.M., Enzyme Microb. Technol., 1998, vol. 23, nos. 1–2, pp. 64–69.
Kim, M.G. and Lee, S.B., J. Mol. Catal., 1996, vol. 1, no. 2, pp. 71–80.
Kim, M.G. and Lee, S.B., J. Mol.Catal. B Enzym., 1996, vol. 1, nos. 3–6, pp. 181–190.
Kurochkina, V.B. and Nys, P.S., Antibiot. Khimioter., 1999, vol. 44, no. 5, pp. 12–16.
Ulijn, R.V., De Martin, L., Halling, P.J., Moore, B.D., and Janssen, A.E.M., J. Biotechnol., 2002, vol. 99, no. 3, pp. 215–222.
Nierstrasz, V.A., Schroen, C.G.P.H., Bosma, R., Kroon, P.G., Beeftink, H.H., and Janssen, A.E.M., Biocatal. Biotransform., 1999, vol. 17, no. 3, pp. 209–224.
Terreni, M., Ubiali, D., Pagani, G., Hernandez-Justiz, O., Fernández-Lafuente, R., and Guisan, J.M., Enzyme Microb. Technol., 2005, vol. 36, nos 5–6, pp. 672–679.
Kurochkina, V.B. and Sklyarenko, A.V., in Biotechnology State of the Art and Prospects for Development., Zaikov, G.E., Ed., Hauppauge, New York: Nova Science Publishers, 2008, ch. 20, pp. 175–204.
Shaw, S., Shyu, J., Hsieh, Y., and Yeh, H., Enzyme Microb. Technol., 2000, vol. 26, nos. 2–4, pp. 142–151.
Nys, P.S., Kurochkina, V.B., and Libinson, G., in IMACS/IFAC First Symp. Math. Model Simul. Agric. Bio-industries, Brussel, Belgium, 1995, vol. IV, pp. B3–1, B3–5.
Kurochkina, V.B., Larina, E.V., Libinson, G.S., and Nys, P.S., Antibiot. Khimioter., 1994, vol.39, no. 12, pp. 3–7.
Won, J.I., Kim, C.G., Kim, J.H., Lee, J.H., and Jeon, Y.J., Appl. Biochem. Biotechnol., 1998, vol. 69, no. 1, pp. 1–9.
Park, C.B., Lee, S.B., and Ryu, D.D., J. Mol. Catal., 2000, vol. 9, nos. 4–6, pp. 275–281.
Fernandez-Lafuente, R., Guisán, J., Pregnolato, M., and Terreni, M., Tetrahedron Lett., 1997, vol. 38, no. 26, pp. 4693–4696.
Hernandez-Justiz, O., Fernandez-Lafuente, R., Guisan, J.M., Negri, P., Pagani, G., and Pregnolato, M., Org. Chem., 1997, vol. 62, no. 26, pp. 9099–9106.
Klesov, A.A., Margolin, A.L., and Shvyadas, V.K., Bioorg. Khim., 1977, vol. 3, no. 5, pp. 654–662.
RF Patent no. 2210596, 2000.
Terreni, M., Pagani, G., Ubiali, D., Fernández-Lafuente, R., Mateo, C., and Guisan, J.M., Bioorg. Med. Chem. Lett., 2001, vol. 11, no. 18, pp. 2429–2432.
Fernández-Lafuente, R., Rosell, C.M., and Guisan, J.M., Enzyme Microb. Technol., 1998, vol. 23, no. 5, pp. 305–310.
Terreni, M., Tchamkam, J., Sarnataro, U., Rocchietti, S., Fernandez-Lafuente, R., and Guisán, J.M., Adv. Synth. Catal., 2005, vol. 347, no. 1, pp. 121–128.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © A.V. Sklyarenko, M.A. El’darov, V.B. Kurochkina, S.V. Yarotsky, 2015, published in Prikladnaya Biokhimiya i Mikrobiologiya, 2015, Vol. 51, No. 6, pp. 546–560.
Rights and permissions
About this article
Cite this article
Sklyarenko, A.V., El’darov, M.A., Kurochkina, V.B. et al. Enzymatic synthesis of β-lactam acids (review). Appl Biochem Microbiol 51, 627–640 (2015). https://doi.org/10.1134/S0003683815060150
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0003683815060150