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Applied and Environmental Microbiology, June 2006, p. 4382-4387, Vol. 72, No. 6
0099-2240/06/$08.00+0     doi:10.1128/AEM.00380-06
Copyright © 2006, American Society for Microbiology. All Rights Reserved.

Structure of Trichamide, a Cyclic Peptide from the Bloom-Forming Cyanobacterium Trichodesmium erythraeum, Predicted from the Genome Sequence

Sebastian Sudek,¹ Margo G. Haygood,^1,2 Diaa T. A. Youssef,³ and Eric W. Schmidt^4*

Scripps Institution of Oceanography, University of California—San Diego, La Jolla, California,¹ Department of Environmental and Biomolecular Systems, OGI School of Science and Engineering, Oregon Health and Science University, Beaverton, Oregon,² Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia, Egypt,³ Department of Medicinal Chemistry, University of Utah, Salt Lake City, Utah⁴

Received 15 February 2006/ Accepted 6 April 2006

A gene cluster for the biosynthesis of a new small cyclic peptide, dubbed trichamide, was discovered in the genome of the global, bloom-forming marine cyanobacterium Trichodesmium erythraeum ISM101 because of striking similarities to the previously characterized patellamide biosynthesis cluster. The tri cluster consists of a precursor peptide gene containing the amino acid sequence for mature trichamide, a putative heterocyclization gene, an oxidase, two proteases, and hypothetical genes. Based upon detailed sequence analysis, a structure was predicted for trichamide and confirmed by Fourier transform mass spectrometry. Trichamide consists of 11 amino acids, including two cysteine-derived thiazole groups, and is cyclized by an NC terminal amide bond. As the first natural product reported from T. erythraeum, trichamide shows the power of genome mining in the prediction and discovery of new natural products.

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* Corresponding author. Mailing address: Department of Medicinal Chemistry, University of Utah, 30 South 2000 East, Room 201, Salt Lake City, UT 84112. Phone: (801) 585-5234. Fax: (801) 585-9119. E-mail: ews1{at}utah.edu.

Supplemental material for this article may be found at http://aem.asm.org/.

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Applied and Environmental Microbiology, June 2006, p. 4382-4387, Vol. 72, No. 6
0099-2240/06/$08.00+0     doi:10.1128/AEM.00380-06
Copyright © 2006, American Society for Microbiology. All Rights Reserved.

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