1887

Abstract

Neutral L-amino acids were added to liquid cultures of pv. that were entering the exponential phase of growth. For each amino acid addition experiment the production of the usual coronafacoyl compounds, coronatine and -coronafacoyl-L-valine, was diminished and a new product was detected. This was isolated and purified, and established by mass spectrometry and GC analysis of the amino acid released by acid hydrolysis to be the -coronafacoyl amide of each L-amino acid added to the culture. Coupling was established to occur between coronafacic acid and the L-amino acids alanine, ?-aminobutyric acid, norvaline, isoleucine, alloisoleucine, leucine and norleucine. These results suggest that an intracellular enzyme system is operating which lacks an overall rigid specificity in the coupling (amide bond formation) between coronafacic acid and aliphatic neutral amino acids.

Loading

Article metrics loading...

/content/journal/micro/10.1099/00221287-132-6-1503
1986-06-01
2024-04-23
Loading full text...

Full text loading...

/deliver/fulltext/micro/132/6/mic-132-6-1503.html?itemId=/content/journal/micro/10.1099/00221287-132-6-1503&mimeType=html&fmt=ahah

References

  1. Gottschalk G. 1979; Regulation of bacterial metabolism.. In Bacterial Metabolism pp 142–166 editor Starr M. P. New York: Springer-Verlag;
    [Google Scholar]
  2. Hoitink H. A. J., SINDEN S. L. 1970; Partial purification and properties of chlorosis-inducing toxins of Pseudomonas phaseolicola and Pseudomonas glycinea. . Phytopathology 60:1236–1237
    [Google Scholar]
  3. ICHIHARA A., SHIRAISHI K., SATO H., SAKAMURA S., NISHIYAMA K., SAKAI R., FURUSAKI A., MATSUMOTO T. 1976; The structure of coronatine.. Journal of the American Chemical Society 99:636
    [Google Scholar]
  4. Mitchell R. E. 1982; Coronatine production by some phytopathogenic pseudomonads.. Physiological Plant Pathology 20:83–89
    [Google Scholar]
  5. Mitchell R. E. 1984; A naturally occurring structural analogue of the phytotoxin coronatine.. Phytochemistry 23:791–793
    [Google Scholar]
  6. Mitchell R. E. 1985a; Norcoronatine and iV-coronafacoyl-L-valine, phytotoxic analogues of coronatine produced by a strain of Pseudomonas syringae pv. glycinea. . Phytochemistry 24:1485–1488
    [Google Scholar]
  7. Mitchell R. E. 1985b; Coronatine biosynthesis: incorporation of L-[U-14C]isoleucine and L-[U- 14C]threonine into the l-amido-l-carboxy-2-ethyl- cyclopropyl moiety. . Phytochemistry 24:247–249
    [Google Scholar]
  8. Mitchell R. E., Young H. 1985; N-Corona- facoyl-L-isoleucine and N-coronafacoyl-L-alloiso- leucine, potential biosynthetic intermediates of the phytotoxin coronatine. . Phytochemistry 24:2716–2717
    [Google Scholar]
  9. Shiraishi K., Konoma K., Sato H., Ichihara A., Sakamura S., Nishiyama K., Sakai R. 1979; The structure-activity relationships in coronatine analogs and amino compounds derived from ( + )- coronafacic acid. . Agricultural and Biological Chemistry 43:1753–1757
    [Google Scholar]
http://instance.metastore.ingenta.com/content/journal/micro/10.1099/00221287-132-6-1503
Loading
/content/journal/micro/10.1099/00221287-132-6-1503
Loading

Data & Media loading...

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error