Abstract
Studies with 14C-labeled isoleucine stereisomers have established that l-alloisoleucine, d-alloisoleucine, and d-isoleucine may function as precursors for the biogenesis of d-isoleucine and N-methyl-l-alloisoleucine residues in actinomycin. l-[14C]isoleucine appears to be employed chiefly for d-alloisoleucine (and N-methylisoleucine [?] formation); however, its role in the biosynthesis of d-isoleucine and N-methylalloisoleucine remains unclear. The potential pathway of biosynthesis of d-isoleucine and N-methyl-l-isoleucine is discussed.
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Selected References
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- ALBERTINI A., CASSANI G., CIFERRI O. INCORPORATION OF L-ISOLEUCINE AND L-THREONINE INTO THE ACTINOMYCINS SYNTHESIZED BY STREPTOMYCES ANTIBIOTICUS. Biochim Biophys Acta. 1964 Apr 27;80:655–664. doi: 10.1016/0926-6550(64)90310-x. [DOI] [PubMed] [Google Scholar]
- BODANSZKY M., PERLMAN D. ARE PEPTIDE ANTIBIOTICS SMALL PROTEINS? Nature. 1964 Nov 28;204:840–844. doi: 10.1038/204840a0. [DOI] [PubMed] [Google Scholar]
- Bodanszky M., Perlman D. Origin of D-amino-acids in microbial peptides: rule of alpha-epimerization. Nature. 1968 Apr 20;218(5138):291–292. doi: 10.1038/218291a0. [DOI] [PubMed] [Google Scholar]
- Brady L. R. Toxins of higher fungi. Lloydia. 1975 Jan-Feb;38(1):36–56. [PubMed] [Google Scholar]
- Bycroft B. W. Structural relationships in microbial peptides. Nature. 1969 Nov 8;224(5219):595–597. doi: 10.1038/224595a0. [DOI] [PubMed] [Google Scholar]
- DIGIROLAMO M., CIFERRI O., DIGIROLAMO A. B., ALBERTINI A. EFFECT OF D-LEUCINE ON THE BIOSYNTHESIS OF POLYMIXIN D. J Biol Chem. 1964 Feb;239:502–507. [PubMed] [Google Scholar]
- Hook D. J., Vining L. C. Biosynthetic precursors of etamycin, a peptidolactone antibiotic from Streptomyces griseoviridus. Can J Biochem. 1973 Dec;51(12):1630–1637. doi: 10.1139/o73-219. [DOI] [PubMed] [Google Scholar]
- KATZ E., GOSS W. A. Controlled biosynthesis of actinomycin with sarcosine. Biochem J. 1959 Nov;73:458–465. doi: 10.1042/bj0730458. [DOI] [PMC free article] [PubMed] [Google Scholar]
- KATZ E. Influence of valine, isoleucine, and related compounds on actinomycin synthesis. J Biol Chem. 1960 Apr;235:1090–1094. [PubMed] [Google Scholar]
- KATZ E., PIENTA P., SIVAK A. The role of nutrition in the synthesis of actinomycin. Appl Microbiol. 1958 Jul;6(4):236–241. doi: 10.1128/am.6.4.236-241.1958. [DOI] [PMC free article] [PubMed] [Google Scholar]
- KATZ E., WALDRON C. R., MELONI M. L. Role of valine and isoleucine as regulators of actinomycin peptide formation by Streptomyces chrysomallus. J Bacteriol. 1961 Oct;82:600–608. doi: 10.1128/jb.82.4.600-608.1961. [DOI] [PMC free article] [PubMed] [Google Scholar]
- KATZ E., WEISSBACH H. Incorporation of C14-labeled amino acids into actinomycin and protein by Streptomyces antibioticus. J Biol Chem. 1963 Feb;238:666–675. [PubMed] [Google Scholar]
- Katz E., Kawai Y., Jun'ichi S. Configuration of the N-methylisoleucine in the actinomycins. Biochem Biophys Res Commun. 1971 Jun 4;43(5):1035–1039. doi: 10.1016/0006-291x(71)90566-3. [DOI] [PubMed] [Google Scholar]
- Lipmann F., Gevers W., Kleinkauf H., Roskoski R., Jr Polypeptide synthesis on protein templates: the enzymatic synthesis of gramicidin S and tyrocidine. Adv Enzymol Relat Areas Mol Biol. 1971;35:1–34. doi: 10.1002/9780470122808.ch1. [DOI] [PubMed] [Google Scholar]
- MACDONALD J. C. Biosynthesis of valinomycin. Can J Microbiol. 1960 Feb;6:27–34. doi: 10.1139/m60-005. [DOI] [PubMed] [Google Scholar]
- Manning J. M., Moore S. Determination of D- and L-amino acids by ion exchange chromatography as L-D and L-L dipeptides. J Biol Chem. 1968 Nov 10;243(21):5591–5597. [PubMed] [Google Scholar]
- Mauger A. B. Peptide antibiotic biosynthesis: a new approach. Experientia. 1968 Oct 15;24(10):1068–1072. doi: 10.1007/BF02138755. [DOI] [PubMed] [Google Scholar]
- SALZMAN L. A., KATZ E., WEISSBACH H. STUDIES ON THE MECHANISM OF SYNTHESIS OF D-VALINE BY STREPTOMYCES ANTIBIOTICUS. J Biol Chem. 1964 Jun;239:1864–1866. [PubMed] [Google Scholar]
- SIVAK A., MELONI M. L., NOBILI F., KATZ E. Biosynthesis of the actinomycin chromophore. Studies with DL-[7alpha-14C] tryptophan and L-[Me-14C] methionine. Biochim Biophys Acta. 1962 Feb 26;57:283–289. doi: 10.1016/0006-3002(62)91121-6. [DOI] [PubMed] [Google Scholar]
- Schleifer K. H., Kandler O. Peptidoglycan types of bacterial cell walls and their taxonomic implications. Bacteriol Rev. 1972 Dec;36(4):407–477. doi: 10.1128/br.36.4.407-477.1972. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Snoke J. E. FORMATION OF BACITRACIN BY PROTOPLASTS OF BACILLUS LICHENIFORMIS. J Bacteriol. 1961 Jun;81(6):986–989. doi: 10.1128/jb.81.6.986-989.1961. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Troy F. A. Chemistry and biosynthesis of the poly( -D-glutamyl) capsule in Bacillus licheniformis. I. Properties of the membrane-mediated biosynthetic reaction. J Biol Chem. 1973 Jan 10;248(1):305–315. [PubMed] [Google Scholar]
- Yajim T., Mason K. T., Kaltz E. Branched-chain amino acid substitutions in the biosynthesis of the antibiotic actinomycin. Antimicrob Agents Chemother. 1975 Jun;7(6):773–780. doi: 10.1128/aac.7.6.773. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Yajima T., Grigg M. A., Katz E. Biosynthesis of antibiotic peptides with isoleucine stereoisomers. Arch Biochem Biophys. 1972 Aug;151(2):565–575. doi: 10.1016/0003-9861(72)90534-6. [DOI] [PubMed] [Google Scholar]
