Skip to main content
NCBI home page
Antimicrobial Agents and Chemotherapy logoLink to Antimicrobial Agents and Chemotherapy
. 1979 Sep;16(3):392–397. doi: 10.1128/aac.16.3.392

Isolation and nature of intracellular alpha-aminoadipic acid-containing peptides from Paecilomyces persicinus P-10.

L A Eriquez, M A Pisano
PMCID: PMC352866  PMID: 574371

Abstract

Small intracellular peptides containing alpha-aminoadipic acid, cysteine, and a valine moiety were obtained from mycelia of Paecilomyces persicinus P-10 by ethanol or trichloroacetic acid extraction. After performic acid oxidation and ion-exchange chromatography, analysis of the peptide fractions by two-dimensional thin-layer electrophoresis and chromatography revealed the presence of three related peptides, as sulfonic acid derivatives, each containing alpha-aminoadipic acid. Each peptide was isolated in chromatographically pure form by semipreparative thin-layer electrophoresis and chromatography. The purified peptides were subjected to differential hydrolysis, dansylation, and combined dansylation-phenylisothiocyanate sequence analysis. Based on these studies, the structures of the isolated peptides were determined to be (i) glycl-delta-(alpha-aminoadipyl)-cysteinyl-beta-hydroxyvaline, (ii) glycyl-delta-(alpha-aminoadipyl)-cysteinylvaline, and (iii) delta-(alpha-aminoadipyl)-cysteinylvaline. The peptides isolated from Paecilomyces are similar to the alpha-aminoadipic acid-cysteine-valine moiety complex peptides isolated from Cephalosporium.

Full text

PDF
392

Selected References

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

  1. ARNSTEIN H. R., ARTMAN M., MORRIS D., TOMS E. J. Sulphur-containing amino acids and peptides in the mycelium of Penicillium chrysogenum. Biochem J. 1960 Aug;76:353–357. doi: 10.1042/bj0760353. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. 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]
  3. Arnott M. S., Ward D. N. Separation of dansyl amino acids in a single analysis. Anal Biochem. 1967 Oct;21(1):50–56. doi: 10.1016/0003-2697(67)90082-6. [DOI] [PubMed] [Google Scholar]
  4. Chan J. A., Huang F. C., Sih C. J. The absolute configuration of the amino acids in delta-(alpha-aminoadipyl)cysteinylvaline from Penicillium chrysogenum. Biochemistry. 1976 Jan 13;15(1):177–180. doi: 10.1021/bi00646a027. [DOI] [PubMed] [Google Scholar]
  5. Cole M., Fletcher J. C., Robson A. The separation of 1-dimethylaminonaphthalene-5-sulphonamido acids (DNS-amino acids) by thin-layer chromatography. J Chromatogr. 1965 Dec;20(3):616–618. doi: 10.1016/s0021-9673(01)97475-8. [DOI] [PubMed] [Google Scholar]
  6. D'Amato R. F., Pisano M. A. A chemically defined medium for cephalosporin C production by Paecilomyces persicinus. Antonie Van Leeuwenhoek. 1976;42(3):299–308. doi: 10.1007/BF00394127. [DOI] [PubMed] [Google Scholar]
  7. Demain A. L. Biochemistry of penicillin and cephalosporin fermentations. Lloydia. 1974 Jun;37(2):147–167. [PubMed] [Google Scholar]
  8. Gray W. R., Smith J. F. Rapid sequence analysis of small peptides. Anal Biochem. 1970 Jan;33(1):36–42. doi: 10.1016/0003-2697(70)90436-7. [DOI] [PubMed] [Google Scholar]
  9. Gros C., Labouesse B. Study of the dansylation reaction of amino acids, peptides and proteins. Eur J Biochem. 1969 Feb;7(4):463–470. doi: 10.1111/j.1432-1033.1969.tb19632.x. [DOI] [PubMed] [Google Scholar]
  10. Inglis A. S., Liu T. Y. The stability of cysteine and cystine during acid hydrolysis of proteins and peptides. J Biol Chem. 1970 Jan 10;245(1):112–116. [PubMed] [Google Scholar]
  11. Loder P. B., Abraham E. P., Newton G. G. Behaviour of alpha-aminoadipylcysteine and glutamylcysteine in the presence of intact and disrupted mycelium of a Cephalosporium sp. Biochem J. 1969 May;112(4):389–396. doi: 10.1042/bj1120389. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. NEWTON G. G., ABRAHAM E. P. Degradation, structure and some derivatives of cephalosporin N. Biochem J. 1954 Sep;58(1):103–111. doi: 10.1042/bj0580103. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Nedkov P., Genov N. A method for identifying C-terminal amino acids as their DNS-derivatives obtained after the hydrazinolysis of peptides. Biochim Biophys Acta. 1966 Oct 31;127(2):544–545. doi: 10.1016/0304-4165(66)90413-2. [DOI] [PubMed] [Google Scholar]
  14. Perrett D., Webb J. P., Silk D. B., Clark M. L. The assay of dipeptides using fluorescamine and its application to determining dipeptidase activity. Anal Biochem. 1975 Sep;68(1):161–166. doi: 10.1016/0003-2697(75)90690-9. [DOI] [PubMed] [Google Scholar]
  15. Pisano M. A., Vellozzi E. M. Production of cephalosporin C by Paecilomyces persicinus P-10. Antimicrob Agents Chemother. 1974 Oct;6(4):447–451. doi: 10.1128/aac.6.4.447. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Sargent J. R., Vadlamudi B. P. Electrophoresis of peptides on thin layers of silica gel. Anal Biochem. 1968 Oct 24;25(1):583–587. doi: 10.1016/0003-2697(68)90137-1. [DOI] [PubMed] [Google Scholar]
  17. Stapley E. O., Jackson M., Hernandez S., Zimmerman S. B., Currie S. A., Mochales S., Mata J. M., Woodruff H. B., Hendlin D. Cephamycins, a new family of beta-lactam antibiotics. I. Production by actinomycetes, including Streptomyces lactamdurans sp. n. Antimicrob Agents Chemother. 1972 Sep;2(3):122–131. doi: 10.1128/aac.2.3.122. [DOI] [PMC free article] [PubMed] [Google Scholar]
  18. Tichy H. Chromatography of dansyl-peptides from tryptic digests of electrophoretically separated proteins. Anal Biochem. 1975 Dec;69(2):552–557. doi: 10.1016/0003-2697(75)90160-8. [DOI] [PubMed] [Google Scholar]
  19. Woods K. R., Wang K. T. Separation of dansyl-amino acids by polyamide layer chromatography. Biochim Biophys Acta. 1967 Feb 21;133(2):369–370. doi: 10.1016/0005-2795(67)90078-5. [DOI] [PubMed] [Google Scholar]

Articles from Antimicrobial Agents and Chemotherapy are provided here courtesy of American Society for Microbiology (ASM)

RESOURCES