Adipoyl-6-aminopenicillanic acid is a substrate for deacetoxycephalosporin C synthase (DAOCS)

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 13, 1996, Pages 1579-1584

  Shibata, Norio ^a   Lloyd, Matthew D ^a   Baldwin, Jack E ^a   Schofield, Christopher J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

6 AMINOPENICILLANIC ACID; ADICILLIN; CEPHALOSPORIN; DEACETOXYCEPHALOSPORIN C;

ACETYLATION; ARTICLE; BACTERIAL METABOLISM; BIOSYNTHESIS; HYDROXYLATION; STREPTOMYCES CLAVULIGERUS;

BACTERIA (MICROORGANISMS); FELIS CATUS; STREPTOMYCES CLAVULIGERUS;

EID: 0030576318     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00278-8     Document Type: Article

References (26)

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13. 3 in 2% (v/v) methanol, 1 mL/min, λ = 218 nm).
14. 10. Lloyd, M. D., Schofield, C. J. and Baldwin, J. E., manuscript in preparation.
15. +, 100%).
16. cat was calculated using a mass for DAOCS of 34,500 Da.
17. 13 a). Kovacevic, S., Weigal, B. J., Tobin, M. B., Ingold, T. D. and Miller, J. R., J. Bacteriol., 1989, 171, 754-760;
18. b). Morgan, N., Pereira, I. A. C., Andersson, I. A., Adlington, R. M., Baldwin, J. E., Cole, S. C. J., Crouch, N. P. and Sutherland, J. D., Bioorg. Med. Chem. Lett., 1994, 4, 1595-1600.
19. 14. Baldwin, J. E., Schofield, C. J., Smith, B. D., Tetrahedron, 1990, 46, 3019-3028.
20. 15. Reference 2b reports that m-carboxyphenylacetyl-6-APA was expanded by DAOC/DACS to the corresponding cephalosporin at 50% of the rate of penicillin N 1, compared to 40% of the rate of penicillin N 1 for adipoyl-6-APA 5. No data on the expansion of m-carboxyphenylacetyl-6-APA by recombinant DAOCS has been reported.
21. 16a). Baldwin, J. E., Shiau, C.-Y., Byford, M. F. and Schofield, C. J., Biochem. J., 1994, 301, 367-372;
22. b). Zhang, J., Wolfe, S. and Demain, A. L., Biochem. J., 1992, 283, 691-698. Note, although it seems that adipic acid can not (efficiently) substitute for L-α-aminoadipic acid in the ACV synthetase catalysed formation of tripeptides, it can not be ruled out that it stimulates the formation of the dipeptide shunt product. See: Shiau, C.-Y., Baldwin, J. E., Byford, M. F., and Schofield, C. J., FEBS lett., 1995, 373, 303-306.
23. b). Zhang, J., Wolfe, S. and Demain, A. L., Biochem. J., 1992, 283, 691-698. Note, although it seems that adipic acid can not (efficiently) substitute for L-α-aminoadipic acid in the ACV synthetase catalysed formation of tripeptides, it can not be ruled out that it stimulates the formation of the dipeptide shunt product. See: Shiau, C.-Y., Baldwin, J. E., Byford, M. F., and Schofield, C. J., FEBS lett., 1995, 373, 303-306.
24. 17. Alvi, K. A., Reeves, C. D., Peterson, J. and Lein, J., J. Antibiot., 1995, 48, 338-340.
25. 17 suggest that hydroxyadipoyl-7-ADCA 9 was produced via ring expansion of 16-hydroxyadipoyl-6-APA 10. However, it is also possible that 9 arises via metabolism of DAOC 2.
26. 19. Bradford, M. M., Anal. Biochem., 1976, 72, 248-254.