Chemoenzymatic one-pot synthesis of cefazolin from cephalosporin C in fully aqueous medium, involving three consecutive biotransformations catalyzed by D-aminoacid oxidase, glutaryl acylase and penicillin G acylase

Tetrahedron Letters

Volumn 38, Issue 26, 1997, Pages 4693-4696

  Fernández Lafuente, Roberto ^a   Guisán, José M ^a   Pregnolato, Massimo ^b   Terreni, Marco ^b  

^a CSIC   (Spain)

^b UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDASE; AMINO ACID OXIDASE; CEFAZOLIN; CEPHALOSPORIN C;

ACYLATION; ARTICLE; BIOTRANSFORMATION; CHEMICAL REACTION; DRUG PURIFICATION; DRUG SYNTHESIS;

EID: 0141954380     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00999-4     Document Type: Article

References (16)

1. Nakano, H. in Pharmacological and Biochemical Properties of Drug Substances. Goldberg, M. E. Ed (Am. Pharm. Assoc., Washington, DC, USA) 1977, p. 155.
2. Dürckheimer, W.; Blumbach, J.; Lattrel, R. and Scheunemann, K.H. Angew. Chem. Ed. Engl. 1985, 24, 180.
3. Sogli, L.; Terrassan, D. and Ribaldone, G. U.S. Patent. 5387679, 1995.
4. (a) Sonawane, V.C., Jolly, R.S. and Vohra, R.M., Biotechnology Lett.. 1996, 18, 965.
5. (b) Croux, C.; Perez, J.C.; Fuentes, J.L.B, and Maldonado, F.S. U.S. Patent. 5354667, 1994.
6. (c) Aramori, I.; Fukagawa, M.; Ono, H.; Ishitani, Y.; Tsumura, M.; Iwami, M. and Kojo, H. U.S. Patent. 5310659, 1994.
7. (d) Aramori, I.; Fukagawa, M.; Ono, H.; Ishitani, Y.; Tsmura, M.; Iwami, M. and Kojo, H. U.S. Patent. 5312750, 1994.
8. (e) Battistel, E. A.; Cesti, P.; Franzosi, G.; van der Goes, V.; Bonicelli, S. and Pilone, M. U.S. Patent. 5296358, 1994.
9. (a) Kasche, V.; Haufler, U. and Riechman, L. Meth. Enzymol. 1987, 136, 280.
10. (b) Kasche, V. Enzyme Microb.Technol. 1986, 8, 4.
11. (c) Sadvige, T.A. in Biotechnology of Industrial Antibiotics, Vandamme, E.J. Ed (Marcell Dekker co., New York N.Y. USA) 1984, p. 171.
12. (d) Okachi, R; Hashimoto, Y.; Kawamori, M.; Katsumata, R.; Takayama, K. And Nara T. in Enzyme Engineering VI, Chibata I.; Fukui, S. and Wingard, L. Eds (Plenum Press, New York, USA) 1983, p. 877.
13. The utilized PGA was isolated from a strain of Escherichia coli ATCC 11105 of industrial provenience (Antibioticos S.A. Leon, Spain), produced from E. coli ATCC 11105 submitted to conventional mutagenesis (e.g., chemical), in order to obtain an hyper-producer strain, and stabilized by covalent multiple-point attachment on activated agarose beads performed as previously described: Guisán J.M.; Fernández-Lafuente, R.; Rodriguez, V.; Bastida, A.; Blanco, R.M.. and Alvaro, G. in Stability and Stabilization of Enzymes; van den Tweel, W.J.J.; Harder, A. and Buitelaar, R.M., Editors (Elsevier Science Publishers, The Netherlands) 1993 pp. 55.
14. (b) Alvaro, G.; Fernández-Lafuente, R.; Blanco R.M. and Guisán J.M Appl. Biochem. Biotechnol. 1990, 26, 181.
15. (c)Guisan, J.M. Enzyme Microb. Technol. 1988, 10, 375.
16. Guisán, J.M.; Rodriguez, V.; Fernández-Lafuente, R.; Bastida A. and Ceinos, P. Spanish patent 9500369, 1995.