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

ABSTRACT 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 N—C 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.

[1]  P. Long,et al.  Spontaneity in the patellamide biosynthetic pathway. , 2006, Organic & biomolecular chemistry.

[2]  B. Moore.  Biosynthesis of marine natural products: macroorganisms (Part B). , 2005, Natural product reports.

[3]  B. Moore.  Biosynthesis of marine natural products: macroorganisms (Part B). , 2005, Natural product reports.

[4]  M. G. Pinho,et al.  Bacterial Cell Wall Synthesis: New Insights from Localization Studies , 2005, Microbiology and Molecular Biology Reviews.

[5]  Y. Igarashi,et al.  Cloning and characterization of the goadsporin biosynthetic gene cluster from Streptomyces sp. TP-A0584. , 2005, Microbiology.

[6]  Sylvie Lautru,et al.  Discovery of a new peptide natural product by Streptomyces coelicolor genome mining , 2005, Nature chemical biology.

[7]  J. Eisen,et al.  Patellamide A and C biosynthesis by a microcin-like pathway in Prochloron didemni, the cyanobacterial symbiont of Lissoclinum patella. , 2005, Proceedings of the National Academy of Sciences of the United States of America.

[8]  M. Namikoshi,et al.  Bioactive compounds produced by cyanobacteria , 1996, Journal of Industrial Microbiology.

[9]  Y. Igarashi,et al.  Cloning and characterization of the goadsporin biosynthetic gene cluster from Streptomyces sp . TPA 0584 , 2005 .

[10]  M. Roman,et al.  Toxicity of blooms of the cyanobacterium Trichodesmium to zooplankton , 1992, Journal of Applied Phycology.

[11]  V. Nizet,et al.  Identification of a Streptolysin S-Associated Gene Cluster and Its Role in the Pathogenesis of Streptococcus iniae Disease , 2002, Infection and Immunity.

[12]  David M. Karl,et al.  Dinitrogen fixation in the world's oceans , 2002 .

[13]  S. Tabata,et al.  Complete genomic sequence of nitrogen-fixing symbiotic bacterium Bradyrhizobium japonicum USDA110. , 2002, DNA research : an international journal for rapid publication of reports on genes and genomes.

[14]  G. Vargo,et al.  Iron fertilization and the Trichodesmiumresponse on the West Florida shelf , 2001 .

[15]  W. Gerwick,et al.  Nitrogen-containing metabolites from marine cyanobacteria. , 2001, The Alkaloids. Chemistry and biology.

[16]  F. Schmitz,et al.  New cyclic peptides from the ascidian Lissoclinum patella. , 1998, Journal of natural products.

[17]  N. Kelleher,et al.  ATP/GTP hydrolysis is required for oxazole and thiazole biosynthesis in the peptide antibiotic microcin B17. , 1998, Biochemistry.

[18]  Edward J. Carpenter,et al.  Trichodesmium, a Globally Significant Marine Cyanobacterium , 1997 .

[19]  J. L. San Millán,et al.  Structure and organization of plasmid genes required to produce the translation inhibitor microcin C7 , 1995, Journal of bacteriology.

[20]  P. Tester,et al.  Toxic effect of the bloom-forming Trichodesmium sp. (Cyanophyta) to the copepod Acartia tonsa. , 1994, Natural toxins.

[21]  H. Paerl,et al.  Growth, Nitrogen Fixation, and Spectral Attenuation in Cultivated Trichodesmium Species , 1993, Applied and environmental microbiology.

[22]  W. Carmichael,et al.  Cyanobacteria secondary metabolites--the cyanotoxins. , 1992, The Journal of applied bacteriology.

[23]  E. Carpenter,et al.  A neurotoxic factor associated with the bloom-forming cyanobacterium Trichodesmium. , 1991, Toxicon : official journal of the International Society on Toxinology.

[24]  S. Z. Qasim,et al.  Succession of organisms following Trichodesmium phenomenon , 1979 .

[25]  M. N. Paranaguá,et al.  On the Mecanism of Red Tide of Trichodesmium in Recife Northeastern Brazil, with Some Considerations of the Relation to the Human Disease "Tamandaré Fever". , 1963 .