Abstract
The tetracycline antibiotics, I, are a group of natural products having notable antibacterial activity toward a broad range of pathogenic microorganisms and characterized by very low toxicity to the mammalian hosts of these pathogens. These properties, together with the fact that the compounds are well absorbed and fully active when administered orally, have made the tetracyclines one of the most useful families of chemotherapeutic agents.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Birch, A. J.: Biosynthetic relations of some natural phenolic and enolic compounds. Fortschr. Chem. org. Naturstoffe 14, 186 (1957).
Birch, A. J., J. F. Snell, and P. J. Thomson: Studies in relation to biosynthesis, part Xxviii. Oxytetracycline (Terramycin). J. Chem. Soc. 1962, 425.
Doerschuk, A. P., J. R. D. McCormick, J. J. Goodman, S. A. Szumski, J. A. Growich, P. A. Miller, B. A. Bitler, E. R. Jensen, M. Matrishin, M. A. Petty, and A. S. Phelps: Biosynthesis of the tetracyclines. I. The halide metabolism of Streptomyces auveofaciens mutants. The preparation and characterization of tetracycline, 7-chlorose-tetracycline and 7-bromotetracycline. J. Am. Chem. Soc. 81, 3069 (1959).
Dulaney, E. L., I. Putter, D. Drescher, L. Chaiet, W. J. Miller, F. J. Wolf, and D. Hendlin: Transethylation in antibiotic biosynthesis. I. An ethyl homolog of oxytetracycline. Biochim. et Biophys. Acta 60, 447 (1962).
Gatenbeck, S.: The biosynthesis of oxytetracycline. Biochem. Biophys. Research Commun. 6, 422 (1961).
Goodman, J. J., and P. A. Miller: The effect of antimetabolites on the biosynthesis of tetracyclines. Biotech. Bioeng. 4, 391 (1962).
Hendlin, D., E. L. Dulaney, D. Drescher, T. Cook, and L. Chaiet: Methionine dependence and the biosynthesis of 6-demethylchlortetracycline. Biochim. et Biophys. Acta 58, 635 (1962).
Hochstein, F. A., M. Schach Von Wittenau, F. W. Tanner, and K. Maurai: 2-acetyl-2-decarboxamido-oxytetracycline. J. Am. Chem. Soc. 82, 5934 (1960).
Lynen, F., and M. Tada: Die biochemischen Grundlagen der Polyacetat-Regel. Angew. Chem. 73, 513 (1961).
McCormick, J. R. D., P. A. Miller, J. A. Growich, N. O. Sjolander, and A. P. Doerschuk: Two new tetracycline-related compounds: 7-chloro-5a(11a)-dehydrotetracycline and 5a-epi-tetracycline. A new route to tetracycline. J. Am. Chem. Soc. 80, 5572 (1958).
McCormick, J. R. D., N. O. Sjolander, P. A. Miller, U. Hirsch, N. Arnold, and A. P. Doerschuk: The biological reduction of 7-chloro-5a(11 a)-dehydrotetracycline to 7-chlorotetracycline by Streptomyces aureofaciens. J. Am. Chem. Soc. 80, 6460 (1958).
McCormick, J. R. D., N. O. Sjolander, S. Johnson, and A. P. Doerschuk: Biosynthesis of the tetracyclines. II. Simple, defined media for growth of Streptomyces auveofaciens and elaboration of 7-chlorotetracycline. J. Bacteriol. 77, 475 (1959).
McCormick, J. R. D., P. A. Miller, S. Johnson, N. Arnold, and N. O. S.Olander: Biosynthesis of the tetracyclines. IV. Biological rehydration of the 5a,6-anhydrotetracyclines. J. Am. Chem. Soc. 84, 3023 (1962).
McCormick, J. R. D., S. Johnson, and N. O. Sjolander: Biosynthesis of the tetracyclines. V. Naphthacenic precursors. J. Am. Chem. Soc. 85, 1692 (1963).
McCormick, J. R. D., and W. E. Gardner: U.S. Patent 3, 074, 975 (1963).
Mccormick, J. R. D.: Biosynthesis of the tetracyclines, part 1 and part 2. Papers presented at the Congress for Antibiotics, Prague 1964.
Mccormlcx, J. R. D.: Biosynthesis of the tetracyclines. In: Biogenesis of antibiotic substances ( Z. VanÊK and Z. Hostalek, ed.). Prague: Publ. House of the Czechoslovak Academy of Sciences 1965a.
McCormick, J. R. D., U. Hirsch Joachim, E. R. Jensen, S. Johnson, and N. O. Sjolander: Biosynthesis of the tetracyclines. Vii. 4-hydroxy-6-methylpretetramid, an intermediate accumulated by a blocked mutant of Streptomyces auveofaciens. J. Am. Chem. Soc. 87, 1793 (1965b).
McCormick, J. R. D., and E. R. Jensen: Biosynthesis of the tetracyclines. Viii. Characterization of 4-hydroxy-6-methylpretetramid. J. Am. Chem. Soc. 87, 1794 (1965).
Miller, P. A., J. R. D. McCormick, and A. P. Doerschuk: Studies of chlortetracycline biosynthesis and the preparation of chlortetracycline-C14. Science 123, 1030 (1956).
Miller, P. A., N. O. Sjolander, S. Nalesnyk, N. Arnold, A. P. Doerschuk, and J. R. D. McCormick: Cosynthetic factor I, a factor involved in hydrogen-transfer in Streptomyces auveofaciens. J. Am. Chem. Soc. 82, 5002 (1960).
Miller, P. A., A. Saturnelli, J. H. Martin, L. A. Mitscher, and N. Bohonos: A new family of tetracycline precursers: N-demethylanhydrotetracyclines. Biochem. Biophys. Research Commun. 16, 285 (1964a).
Miller, P. A., and A. Saturnelli: Terminal reactions in the biosynthesis of tetracyclines. Paper presented at the Second Internat. Fermentation Symposium, London 1964b.
Miller, P. A., J. H. Hash, M. Lincxs, and N. Boxonos: Biosynthesis of 5-hydroxytetracycline. Biochem. Biophys. Research Commun. 18, 325 (1965).
Mindlin, S.Z., and S. I. Alikhanyan: Doklady Akad. Nauk S. S. S.R. 111, 884 (1956).
Perlman, D., L. J. Heuser, J. B. Semar, W. R. Frazier, and J. A. Boska: Process for biosynthesis of 7-chloro-6-demethyltetracycline. J. Am. Chem. Soc. 83, 4481 (1961).
Petty, M. A.: An introduction to the origin and biochemistry of microbial halometabolites. Bacteriol. Rev. 25, 111 (1961).
Scott, A. I., and C. T. Bedford: Simulation of biosynthesis of tetracyclines. A partial synthesis of tetracycline from anhydroaureomycin. J. Am. Chem. Soc. 82, 2271–2272 (1962).
Snell, J. F., A. J. Birch, and P. J. Thomson: The biosynthesis of tetracycline antibiotics. J. Am. Chem. Soc. 82, 2402 (1960).
Zygmunt, W. A.: Selective inhibition in Streptomyces rimosus. J. Bacteriol. 84, 1126 (1962).
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1967 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
McCormick, J.R.D. (1967). Tetracyclines. In: Gottlieb, D., Shaw, P.D. (eds) Biosynthesis. Antibiotics. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-38441-1_11
Download citation
DOI: https://doi.org/10.1007/978-3-662-38441-1_11
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-662-37650-8
Online ISBN: 978-3-662-38441-1
eBook Packages: Springer Book Archive