Alpha-amino acid ester hydrolases: Properties and applications

Applied Biochemistry and Microbiology

Volumn 49, Issue 8, 2013, Pages 672-694

  Kurochkina, V B ^a   Sklyarenko, A V ^a   Berezina, O V ^a   Yarotskii, S V ^a  

^a STATE RESEARCH INSTITUTE OF GENETICS AND SELECTION OF INDUSTRIAL MICROORGANISMS   (Russian Federation)

Author keywords

amino acid ester hydrolase; aminocephalosporins; aminopenicillins; enzymatic synthesis of antibiotics; valacyclovirase

Indexed keywords

EID: 84887467578     PISSN: 00036838     EISSN: None     Source Type: Journal    
DOI: 10.1134/S0003683813080036     Document Type: Article

References (71)

1. Takahashi, T., Yamazaki, Y., and Kato, K., Biochem. J., 1974, vol. 137, pp. 497-503.
2. Nys, P. S., Kurochkina, V. B., Sklyarenko, A. V., and Veinberg, G. A., Antibiot. Khimioter., 2000, vol. 45, no. 11, pp. 36-42.
3. Schmidt, F. R., in The Mycota, 2nd ed., Hofrichter, M., Ed., Berlin Heidelberg: Springer-Verlag, 2010, vol. 10, Ch. 5, pp. 101-121.
4. DSM internet site: www. dsm. com/en-US/cworld/pub-lic/home/pages/home. jsp.
5. Barends, T. R. M., Polderman-Tijmes, J. J., Jekel, P. A., Williams, C., Wybenga, G., Janssen, D. B., and Dijkstra, B. W., J. Biol. Chem., 2006, vol. 281, pp. 5804-5810.
6. Blum, J. K., and Bommarius, A. S., J. Mol. Catal. B: Enzym., 2010, vol. 67, pp. 21-28.
7. Burnette, T. C., Harrington, J. A., Rear-Don, J. E., Merrill, B. M., and de Miranda, P., J. Biol. Chem., 1995, vol. 270, pp. 15827-15831.
8. Kim, I., X.-Y. Chu, Kim, S., Provoda, C. J., Lee, K-D., and Amidon, G. L., J. Biol. Chem., 2003, vol. 278, pp. 25348-25356.
9. Kim, I., Song, X., Vig, B. S., Mittal, S., Shin, H. C., Lorenzi, P. J., and Amidon, G. L., Mol. Pharmaceutics, 2004, vol. 1, pp. 117-127.
10. Lai, L., Z. Xu, J. Zhou, K-D. Lee, G. L. Amidon, J. Biol. Chem., 2008, vol. 283, pp. 9318-9327.
11. Takahashi, T., Yamazaki, Y., Kato, K., and Isono, M., J. Am. Chem. Soc., 1972, vol. 94, pp. 4035-4037.
12. Kato, K., Kato, K., Kawahara, K., and Takahashi, T., Agric. Biol. Chem., 1980, vol. 44, pp. 821-825.
13. Okachi, R., Okachi, R., Kato, K., Miyamura, Y., and Nara, T., Agric. Biol. Chem., 1973, vol. 37, pp. 1953-1957.
14. Okachi, R., Okachi, R., and Nara, T., Agric. Biol. Chem., 1973, vol. 37, pp. 2797-2804.
15. Shimizu, M., Masuike, T., Fujita, H., Kimura, K., Okachi, R., and Nara, T., Agric. Biol. Chem., 1975, vol. 39, pp. 1225-1232.
16. Kawamori, M., Hashimoto, Y., Katsumata, R., Okachi, R., and Takayama, K., Agric. Biol. Chem., 1983, vol. 47, pp. 2503-2509.
17. Wang, M., Wang, Z., Yue, H., Han, W., and Jiao, Q., Wei Sheng Wu Xue Bao, 1990, vol. 30, pp. 238-241.
18. Penzikova, G. A., Oreshina, M. G., and Kuznetsova, V. D., Antibiotiki, 1980, vol. 25, pp. 905-909.
19. Ryu, Y. W., and Ryu, D. Y., Enzyme Microb. Technol., 1987, vol. 9, pp. 339-344.
20. Kim, D. J. and Byun, S. M., Biochim. Biophys. Acta, Prot. Struc. Mol. Enzymol., 1990, vol. 1040, pp. 12-18.
21. Krest'yanova, I. N., Uvarov, N. N., Rudenskaya, G. N., Tsibanov, V. V., Vasil'eva, L. I., and Stepanov, V. M., Biokhimiya, 1990, vol. 55, pp. 12-18.
22. Blinkovsky, A. M. and Markaryan, A. N., Enzyme Microb. Technol., 1993, vol. 15, pp. 965-973.
23. Zaslavskaya, P. L., Chekalina, I. V., Igans, D. N., Bartoshevich, Y. E., and Nys, P. S., Biotechnol. Appl. Biochem., 1993, vol. 18, pp. 299-309.
24. Choi, W. G., Lee, S. B., and Ryu, D. Y., Biotechnol. Bioeng, 1981, vol. 23, pp. 361-371.
25. Ryu, Y. W., and Ryu, D. Y., Enzyme Microb. Technol., 1988, vol. 10, pp. 239-245.
26. Takahashi, T., Kato, K., Yamazaki, Y., and Isono, M., Jpn. J. Antibiot., 1977, vol. 30, pp. 230-S238.
27. Kato, K., K. Kawahara, T. Takahashi, A. Kakinuma, Agric. Biol. Chem., 1980, vol. 44, pp. 1069-1074.
28. Kato, K., Kawahara, K., Takahashi, T., and Kakinuma, A., Agric. Biol. Chem., 1980, vol. 44, pp. 1075-1081.
29. Kato, K. and Kakinuma, A., Agric. Biol. Chem., 1980, vol. 44, pp. 1663-1664.
30. Nam, D. H. and C. Kim, Biothechnol. Bioeng., 1985, vol. 27, pp. 953-960.
31. Okubo, A., Nagaoka, K., Yokota, S., Konishi, E., and Kakutani, T., Int. Patent No. WO02086127, C12N15/55, C12N15/86, C12N15/88, 2002.
32. Kim, D. J. and Byun, S. M., Biochem. Biophys. Res. Commun., 1990, vol. 166, pp. 904-908.
33. Kuwana, N., Kawamura T., and Fukumura, M., US Patent No. US3716454, A61K31/43, A61K35/74, C07D499/68, C12P1/04, C12P37/02, A61K, C07D, (IPC1-7): C12D9/00, 1973.
34. Nam, D. H., and Ryu, D. D. Y., Kor. J. Appl. Microbiol. Biotechnol., 1988, vol. 16, pp. 363-368.
35. Alonso, J. and Garcia, J. L., Microbiology, 1996, vol. 142, pp. 2951-2957.
36. Polderman-Tijmes, J. J., Jekel, P. A., de Vries, E. J., van Merode, A. E. J., Floris, R., van der Laan, J.-M., Sonke, T., and Janssen, D. B., Appl. Environ. Microbiol., 2002, vol. 68, pp. 211-218.
37. Polderman-Tijmes, J. J., Jekel, P. A., Jeronimus-Stratingh, C. M., Bruins, A. P., van der Laan, J.-M., Sonke, T., and Janssen, D. B., J. Biol. Chem., 2002, vol. 277, pp. 28474-28482.
38. van der Laan, J.-M., Polderman-Tijmes, J. J., and Barends, T. R. M., Int. Patent No. WO02086111, C12N15/55, C12N9/18, (IPC1-7): C12N9/00, 2002.
39. Barends, T. R. M., Polderman-Tijmes, J. J., Jekel, P. A., Hensgens, C. M. H., de Vries, E. J., Janssen, D. B., and Dijkstra, B. W., J. Biol. Chem., 2003, vol. 278, pp. 23076-23084.
40. da Silva, C. R., Ferro, J. A., Reinach, F. C., Farah, C. S., and Furlan, L. R., Nature, 2002, vol. 417, pp. 459-463.
41. Barends, T. R. M., Hensgens, C. M. H., Polderman-Tijmes, J. J., Jekel, P. A., de Vries, E. J., Janssen, D. B., and Dijkstra, B. W., Acta Crystallogr., Sect. D: Biol. Crystallogr., 2003, vol. 59, pp. 158-160.
42. Barends, T. R. M. and Dijkstra, B. W., Acta Crystallogr., Sect. D: Biol. Crystallogr., 2003, vol. 59, pp. 2237-2241.
43. Barends, T. R. M., Yoshida, H., and Dijkstra, B. W., Curr. Opin. Biotechnol., 2004, vol. 15, pp. 356-363.
44. Zarubina, S. A. Uporov, I. V., Fedorchuk, E. A., Fedorchuk, V. V., Sklyarenko, A. V., Yarotskii, S. V. and Tishkov, V. I., Acta Naturae, 2013, vol. 5, no. 3 (in press).
45. Puente, X. S. and Lopez-Oten, C., J. Biol. Chem., 1995, vol. 270, pp. 12926-12932.
46. Kim, I., Crippen, G. M., and Amidon, G. L., Mol. Pharmaceutics, 2004, vol. I, pp. 434-446.
47. Fernandez-Lafuente, R., Hernandez-Justiz, O., Mateo, C., Terreni, M., Alonso, J., Garsia-Lopez, J. L., Moreno, M. A., and Guisan, J. M., J. Mol. Calal. B: Enzym., 2001, vol. 11, pp. 633-638.
48. Deaguero, A. L., Blum, J. K., and Bommarius, A. S., Biocatalytic Synthesis of p-Lactam Antibiotics: Encyclopedia of Industrial Biotechnology: Bioprocess, Bioseparation, and Cell Technology, Flickinger, M. C., Ed., New York: John Wiley and Sons, 2010, pp. 1-32.
49. Krest'yanova, I. N., Vasil'eva, L. I., Denyakina, E. K., Petrova, L. I., Penzikova, G. A., Bartoshevich, Yu. E., and Neklyudov, A. D., Prikl. Biokhim. Mikrobiol., 1985, vol. 21, no. 1, pp. 48-55.
50. Nam, D. H., Ryu, Y. W., and Ryu, D. D. Y., J. Microbiol. Biotechnol., 2001, vol. 11, pp. 329-332.
51. Rhee, D. K, Lee, S. B., Rhee, J. S., Ryu, D. D. Y., and Hospodka, J., Biothechnol. Bioeng., 1980, vol. 22, pp. 1237-1247.
52. Hyun, C. K., Choi, J. H., Kim, J. H., and Ryu, D. D. Y., Biothechnol. Bioeng., 1993, vol. 41, pp. 654-658.
53. Duggleby, H. J., Tolley, S. P., Hill, C. P., Dodson, E. J., and Moody, P. C. E., Nature, 1995, vol. 373, pp. 264-268.
54. Dodson, G. and Wlodawer, A., Trends Biochem. Sci., 1998, vol. 23, pp. 347-352.
55. Hemandez-Justiz, O., Terreni, M., Pagani, G., Garcia, J. L., Guisan, J. M., and Fernandez-Lafuente, R., Enzyme Microb. Technol., 1999, vol. 25, pp. 336-343.
56. Fernandez-Lafuente, R., Hernandez-Justiz, O., Mateo, C., Terreni, M., Fernandez-Lorente, G., Moreno, M. A., Alonso, J., Garcia-Lopez, J. L., and Guisan, J. M., Biomacromolecules, 2001, vol. 2, pp. 95-104.
57. Lee, D. K. and Yoo, D. Y., Korean Patent No. KR810000048, C12P35/04, (IPC1-7): C12P35/04, 1981.
58. Kurochkina, V. B. and Nys, P. S., Antibiot. Khimioter., 1999, vol. 44, no. 8, pp. 6-11.
59. Kurochkina, V. B. and Nys, P. S., Biocatal. Biotransform., 2002, vol. 20, pp. 11-35.
60. Nys, P. S, Kurochkina, V. B., Sklyarenko, A. V., and Egorov, A. M., RF Patent No. RU2221046, C12P37/04, C12N11/02, C12N9/14, C12N11/02, C12RL19, C12RL38, C12RL64, 2004.
61. Sklyarenko, A. V., Kurochkina, V. B., Satarova, D. E., and Krest'yanova, I. N, RF Patent No. RU2381273, C12Nll/00, C12N11/02, C12N19/14, 2009.
62. Xiong Xui, Sklyarenko, A. V., Jiang Yong., Kurochkina, V. B., Hu Yuanhui, and Satarova, D. E., Chinese Patent No. CN101525603, C12N11/02, C12N9/16, C12P35/00, C12P37/00, 2009.
63. Hashimoto, Y., Kimura, K., Kobayashi, S., and Matsukuma, I., US Patent No. US4332896, C07D463/00, C12P17/18, (IPC1-7): C12P17/18, 1982.
64. Ivankin, A. N. and Neklyudov, A. D., Appl. Biochem. Microbiol., 2000, vol. 36, pp. 258-261.
65. Willner, D. and Crast, L. B., Canadian Patent No. CA1044627, C12D9/00, 1978.
66. van der Does, T., Int. Patent No. WO0220819, C12P35/00, C12P37/00, C12P39/00, (IPC1-7): C12P35/02, C12P35/04, C12P37/04, C12P37/06, C12P39/00, 2002.
67. Daka, D., Kim, C. H., Kasahara, S., and Hyun, C. K., Korean Patent No. KR910004952B, C12P35/04, (IPCl-7): C01B33/28, C12P35/04, 1991.
68. Hyun, C. K., Kim, J. H., and Ryu, D. D. Y., Biotechnol. Bioeng., 1993, vol. 42, pp. 800-806.
69. Takeda Chemical Industries Ltd., British Patent GB1382255, C07D499/12, C07D499/64, C07D499/66, 1975.
70. van der Laken, C. J., European Patent EP0339751, C12P37/04, (IPC): C12P37/04, C12P41/00, C12R1/02, 1989.
71. Kurochkina, V. B., Sklyarenko, A. V., Satarova, J. E., and Yarotsky, S. V., Bioprocess Biosyst. Eng., 2011, vol. 34, pp. 1103-1117.