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Applied and Environmental Microbiology, November 2005, p. 6968-6976, Vol. 71, No. 11
0099-2240/05/$08.00+0     doi:10.1128/AEM.71.11.6968-6976.2005
Copyright © 2005, American Society for Microbiology. All Rights Reserved.

Biocatalytic Conversion of Avermectin to 4"-Oxo-Avermectin: Characterization of Biocatalytically Active Bacterial Strains and of Cytochrome P450 Monooxygenase Enzymes and Their Genes

Volker Jungmann,1 István Molnár,2* Philip E. Hammer,2,{dagger} D. Steven Hill,2,{ddagger} Ross Zirkle,2,§ Thomas G. Buckel,1,¶ Dagmar Buckel,1 James M. Ligon,2,{ddagger} and J. Paul Pachlatko1*

Syngenta Crop Protection AG, Schwarzwaldallee 215, CH-4002 Basel, Switzerland,1 Syngenta Biotechnology, Inc., 3054 Cornwallis Rd., Research Triangle Park, North Carolina 277092

Received 3 February 2005/ Accepted 15 July 2005

4"-Oxo-avermectin is a key intermediate in the manufacture of the agriculturally important insecticide emamectin benzoate from the natural product avermectin. Seventeen biocatalytically active Streptomyces strains with the ability to oxidize avermectin to 4"-oxo-avermectin in a regioselective manner have been discovered in a screen of 3,334 microorganisms. The enzymes responsible for this oxidation reaction in these biocatalytically active strains were found to be cytochrome P450 monooxygenases (CYPs) and were termed Ema1 to Ema17. The genes for Ema1 to Ema17 have been cloned, sequenced, and compared to reveal a new subfamily of CYPs. Ema1 to Ema16 have been overexpressed in Escherichia coli and purified as His-tagged recombinant proteins, and their basic enzyme kinetic parameters have been determined.

* Corresponding author. Mailing address for István Molnár: Natural Products Center, Office of Arid Land Studies, University of Arizona, 250 E. Valencia Rd., Tucson, AZ 85706. Phone: (520) 741-1691. Fax: (520) 741-0113. E-mail: imolnar{at}cals.arizona.edu. Mailing address for J. Paul Pachlatko: Bölchenstrasse 21, CH-4411 Seltisberg, Switzerland. Phone: 41 61 911 9953. Fax: 41 61 323 9342. E-mail: pachlatko5{at}bluewin.ch.

{dagger} Present address: Athenix Corp., 2202 Ellis Rd., Suite B, Durham, NC 27702.

{ddagger} Present address: BASF Agricultural Products, 26 Davis Dr., Research Triangle Park, NC 27709.

§ Present address: F. Hoffmann-La Roche, Ltd., Grenzacherstrasse 124, CH-4070 Basel, Switzerland.

Present address: F. Hoffmann-La Roche, Ltd., Grenzacherstrasse 124, CH-4070 Basel, Switzerland.

Applied and Environmental Microbiology, November 2005, p. 6968-6976, Vol. 71, No. 11
0099-2240/05/$08.00+0     doi:10.1128/AEM.71.11.6968-6976.2005
Copyright © 2005, American Society for Microbiology. All Rights Reserved.



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