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Antimicrobial Agents and Chemotherapy, November 2005, p. 4598-4607, Vol. 49, No. 11
0066-4804/05/$08.00+0     doi:10.1128/AAC.49.11.4598-4607.2005
Copyright © 2005, American Society for Microbiology. All Rights Reserved.

Phosphinothricin Tripeptide Synthetases in Streptomyces viridochromogenes Tü494

Dirk Schwartz,1,3 Nicolas Grammel,2 Eva Heinzelmann,1 Ullrich Keller,2* and Wolfgang Wohlleben1*

Mikrobiologie/Biotechnologie, Eberhard-Karls-Universität Tübingen, Auf der Morgenstelle 28, 72076 Tübingen, Germany,1 Institut für Chemie, Arbeitsgruppe Biochemie und Molekulare Biologie, Technische Universität Berlin, Franklinstrasse 29, 10587 Berlin-Charlottenburg, Germany,2 Leibniz-Institut für Naturstoff-Forschung und Infektionsbiologie, Hans-Knöll-Institut, Beutenbergstrasse 11, 07745 Jena, Germany3

Received 24 March 2005/ Returned for modification 14 June 2005/ Accepted 17 August 2005

The tripeptide backbone of phosphinothricin (PT) tripeptide (PTT), a compound with herbicidal activity from Streptomyces viridochromogenes, is assembled by three stand-alone peptide synthetase modules. The enzyme PhsA (66 kDa) recruits the PT-precursor N-acetyl-demethylphosphinothricin (N-Ac-DMPT), whereas the two alanine residues of PTT are assembled by the enzymes PhsB and PhsC (129 and 119 kDa, respectively). During or after assembly, the N-Ac-DMPT residue in the peptide is converted to PT by methylation and deacetylation. Both phsB and phsC appear to be cotranscribed together with two other genes from a single promoter and they are located at a distance of 20 kb from the gene phsA, encoding PhsA, in the PTT biosynthesis gene cluster of S. viridochromogenes. PhsB and PhsC represent single nonribosomal peptide synthetase elongation modules lacking a thioesterase domain. Gene inactivations, genetic complementations, determinations of substrate specificity of the heterologously produced proteins, and comparison of PhsC sequence with the amino terminus of the alanine-activating nonribosomal peptide synthetase PTTSII from S. viridochromogenes confirmed the role of the two genes in the bialanylation of Ac-DMPT. The lack of an integral thioesterase domain in the PTT assembly system points to product release possibly involving two type II thioesterase genes (the1 and the2) located in the PTT gene cluster alone or in conjunction with an as yet unknown mechanism of product release.

* Corresponding author. Mailing address for Wolfgang Wohlleben: Fakultät Biologie, Mikrobiologisches Insitut, Mikrobiologie/Biotechnologie, Auf der Morgenstelle 28, 72076 Tübingen, Germany. Phone: 49 7071 29-76944. Fax: 49 7071 29-5979. E-mail: wolfgang.wohlleben{at}biotech.uni-tuebingen.de. Mailing address for Ullrich Keller: Institut für Chemie, Arbeitsgruppe Biochemie, Technische Universität Berlin, Franklinstrasse 29, 10587 Berlin, Germany. Phone: 49 30 314 25659. Fax: 49 30 314 24783. E-mail: ullrich.keller{at}tu-berlin.de.

Antimicrobial Agents and Chemotherapy, November 2005, p. 4598-4607, Vol. 49, No. 11
0066-4804/05/$08.00+0     doi:10.1128/AAC.49.11.4598-4607.2005
Copyright © 2005, American Society for Microbiology. All Rights Reserved.



This article has been cited by other articles:

  • Eys, S., Schwartz, D., Wohlleben, W., Schinko, E. (2008). Three Thioesterases Are Involved in the Biosynthesis of Phosphinothricin Tripeptide in Streptomyces viridochromogenes Tu494. Antimicrob. Agents Chemother. 52: 1686-1696 [Abstract] [Full Text]  


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