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. 1973 Nov;4(5):542–550. doi: 10.1128/aac.4.5.542

Lysine Biosynthesis in Streptomyces lipmanii: Implications in Antibiotic Biosynthesis

J R Kirkpatrick 1, L E Doolin 1, O W Godfrey 1
PMCID: PMC444592  PMID: 4791488

Abstract

Streptomyces lipmanii produces two β-lactam antibiotics, penicillin N and 7-(5-amino-5-carboxyvaleramido)-7-methoxycephalosporanic acid. Both antibiotics contain α-aminoadipic acid side chains. In similar antibiotics produced by certain fungi, the α-aminoadipoyl moiety is derived from an intermediate in lysine biosynthesis. Our findings indicate, however, that in S. lipmanii, lysine is synthesized via α, ε-diaminopimelic acid—an entirely different biosynthetic route. This finding suggests not only a unique mechanism for the derivation of α-aminoadipate, but also that the system may be particularly amenable to genetic manipulation.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. ARNSTEIN H. R., MORRIS D. The structure of a peptide, containing alpha-aminoadipic acid, cystine and valine, present in the mycelium of Penicillium chrysogenum. Biochem J. 1960 Aug;76:357–361. doi: 10.1042/bj0760357. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Brannon D. R., Mabe J. A., Ellis R., Whitney J. G., Nagarajan R. Origin of glycine from acid hydrolysis of the -lactam antibiotic A16886B. Antimicrob Agents Chemother. 1972 Mar;1(3):242–246. doi: 10.1128/aac.1.3.242. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. CUMMINS C. S., HARRIS H. Studies on the cell-wall composition and taxonomy of Actinomycetales and related groups. J Gen Microbiol. 1958 Feb;18(1):173–189. doi: 10.1099/00221287-18-1-173. [DOI] [PubMed] [Google Scholar]
  4. Dennen D. W., Allen C. C., Carver D. D. Arylamidase of Cephalosporium acremonium and its specificity for cephalosporin C. Appl Microbiol. 1971 May;21(5):907–915. doi: 10.1128/am.21.5.907-915.1971. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Farkas W., Gilvarg C. The reduction step in diaminopimelic acid biosynthesis. J Biol Chem. 1965 Dec;240(12):4717–4722. [PubMed] [Google Scholar]
  6. Grandgenett D. P., Stahly D. P. Diaminopimelate decarboxylase of sporulating bacteria. J Bacteriol. 1968 Dec;96(6):2099–2109. doi: 10.1128/jb.96.6.2099-2109.1968. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Grandgenett D. P., Stahly D. P. Repression of diaminopimelate decarboxylase by L-lysine in different Bacillus species. J Bacteriol. 1971 Mar;105(3):1211–1212. doi: 10.1128/jb.105.3.1211-1212.1971. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. HOARE D. S., WORK E. The stereoisomers of alpha epsilon-diaminopimelic acid. II. Their distribution in the bacterial order Actinomycetales and in certain Eubacteriales. Biochem J. 1957 Mar;65(3):441–447. doi: 10.1042/bj0650441. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. KINDLER S. H., GILVARG C. N-Succinyl-L-2,6-diaminopimelic acid deacylase. J Biol Chem. 1960 Dec;235:3532–3535. [PubMed] [Google Scholar]
  10. Kirkpatrick J. R., Godfrey O. W. The isolation and characterization of auzotrophs of the aspartic acid family from Streptomyces lipmanii. Folia Microbiol (Praha) 1973;18(2):90–101. doi: 10.1007/BF02872830. [DOI] [PubMed] [Google Scholar]
  11. Masurekar P. S., Demain A. L. Lysine control of penicillin biosynthesis. Can J Microbiol. 1972 Jul;18(7):1045–1048. doi: 10.1139/m72-162. [DOI] [PubMed] [Google Scholar]
  12. Miller D. L., Rodwell V. W. Metabolism of basic amino acids in Pseudomonas putida. Catabolism of lysine by cyclic and acyclic intermediates. J Biol Chem. 1971 May 10;246(9):2758–2764. [PubMed] [Google Scholar]
  13. Nagarajan R., Boeck L. D., Gorman M., Hamill R. L., Higgens C. E., Hoehn M. M., Stark W. M., Whitney J. G. Beta-lactam antibiotics from Streptomyces. J Am Chem Soc. 1971 May 5;93(9):2308–2310. doi: 10.1021/ja00738a035. [DOI] [PubMed] [Google Scholar]
  14. PETERKOFSKY B., GILVARG C. N-Succinyl-L-diaminopimelic-glutamic transaminase. J Biol Chem. 1961 May;236:1432–1438. [PubMed] [Google Scholar]
  15. Soda K., Misono H., Yamamoto T. L-Lysine:alpha-ketoglutarate aminotransferase. I. Identification of a product, delta-1-piperideine-6-carboxylic acid. Biochemistry. 1968 Nov;7(11):4102–4109. doi: 10.1021/bi00851a045. [DOI] [PubMed] [Google Scholar]
  16. TROWN P. W., SMITH B., ABRAHAM E. P. Biosynthesis of cephalosporin C from amino acids. Biochem J. 1963 Feb;86:284–291. doi: 10.1042/bj0860284. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. WORK E., DENMAN R. F. The use of a bacterial culture fluid as a source of alpha-diaminopimelic acid. Biochim Biophys Acta. 1953 Jan;10(1):183–183. doi: 10.1016/0006-3002(53)90226-1. [DOI] [PubMed] [Google Scholar]
  18. WORK E. Reaction of ninhydrin in acid solution with straight-chain amino acids containing two amino groups and its application to the estimation of alpha epsilon-diaminopimelic acid. Biochem J. 1957 Nov;67(3):416–423. doi: 10.1042/bj0670416. [DOI] [PMC free article] [PubMed] [Google Scholar]
  19. Whitney J. G., Brannon D. R., Mabe J. A., Wicker K. J. Incorporation of labeled precursors into A16886B, a novel -lactam antibiotic produced by Streptomyces clavuligerus. Antimicrob Agents Chemother. 1972 Mar;1(3):247–251. doi: 10.1128/aac.1.3.247. [DOI] [PMC free article] [PubMed] [Google Scholar]
  20. Yugari Y., Gilvarg C. The condensation step in diaminopimelate synthesis. J Biol Chem. 1965 Dec;240(12):4710–4716. [PubMed] [Google Scholar]

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