Advanced search
Publication Cover
Bioscience, Biotechnology, and Biochemistry Volume 70, 2006 - Issue 12
Journal homepage
151
Views
2
CrossRef citations to date
0
Altmetric
Original Articles

Biosynthetic Origin of [R-(Z)]-4-Amino-3-chloro-2-pentenedioic Acid in Streptomyces viridogenes

Robin I. HUTCHINSONSchool of Biomolecular and Biomedical Science, Centre for Synthesis and Chemical Biology, Ardmore House, University College Dublin
,
Russell J. GRANTSchool of Biomolecular and Biomedical Science, Centre for Synthesis and Chemical Biology, Ardmore House, University College Dublin
&
Cormac D. MURPHYSchool of Biomolecular and Biomedical Science, Centre for Synthesis and Chemical Biology, Ardmore House, University College Dublin
Pages 3046-3049 | Received 30 Jun 2006, Accepted 15 Aug 2006, Published online: 22 May 2014

  • 1) Gribble, G. W., Natural organohalogens: a new frontier for medicinal agents. J. Chem. Ed., 81, 1441–1449 (2004).
  • 2) Keller, S., Wage, T., Hohaus, K., Hölzer, M., Eichhorn, E., and van Pée, K. H., Purification and partial characterisation of tryptophan 7-halogenase (PrnA) from Pseudomonas fluorescens. Angew. Chem. Int. Ed. Engl., 39, 2300–2302 (2000).
  • 3) Vaillancourt, F. H., Yin, J., and Walsh, C. T., SyrB2 in syringomycin E biosynthesis is a nonheme Fe2+ α-ketoglutarate- and O2-dependent enzyme. Proc. Natl. Acad. Sci. USA, 102, 10111–10116 (2005).
  • 4) Murphy, C. D., Recent developments in enzymatic chlorination. Nat. Prod. Rep., 23, 147–152 (2006).
  • 5) Chaiet, L., Arison, B. H., Monaghan, R. L., Springer, J. P., Smith, J. L., and Zimmerman, S. B., [R-(Z)]-4-amino-3-chloro-2-pentenedioic acid, a new antibiotic. Fermentation, isolation and characterisation. J. Antibiotics, 37, 207–210 (1984).
  • 6) Yasuda, N., and Sakane, K., Revised structure and the chemical transformations of FR900148. J. Antibiotics, 44, 801–802 (1991).
  • 7) Culture supernatant was acidified with HCl to pH 3 and any precipitate was removed by filtration; the filtrate was mixed with charcoal (3% w/v) for 10 min, and filtered, and applied to a column of Dowex 50 WX8-100, which was washed with water followed by pyridine (2% v/v). Selected spectroscopic data for 1: 1H NMR (D2O, 500 MHz): δ/ppm 6.8 (s, 1H), 5.1 (s, 1H) (lit. 6.8 (s, 1H), 5.2 (s, 1H)). GC-EIMS data for pertrimethylsilyl derivative of 1: m⁄z=73 (100), 278 (79), 280 (33), 147 (25), 126 (18), 116 (12), 380 (2), 395 (1).
  • 8) Blasiak, L. C., Vaillancourt, F. H., Walsh, C. T., and Drennan, C. T., Crystal structure of the non-haem iron halogenase SyrB2 in syringomycin biosynthesis. Nature, 440, 368–371 (2006).
  • 9) Nowak-Thompson, B., Chaney, N., Wing, J. S., Gould, S. J., and Loper, J. E., Characterization of the pyoluteorin biosynthetic gene cluster of Pseudomonas fluorescens Pf-5. J. Bacteriol., 181, 2166–2174 (1999).
  • 10) Dorrestein, P. C., Yeh, E., Garneau-Tsodikova, S., Kelleher, N. L., and Walsh, C. T., Dichlorination of a pyrrolyl-S-carrier protein by FADH2-dependent halogenase PltA during pyoluteorin biosynthesis. Proc. Natl. Acad. Sci. USA, 102, 13843–13848 (2005).
  • 11) Piraee, M., and Vining, L. C., Use of degenerate primers and touchdown PCR to amplify a halogenase gene fragment from Streptomyces venezuelae ISP5230. J. Ind. Microbiol., 29, 1–5 (2002).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.