Chrysosporide, a Cyclic Pentapeptide from a New Zealand Sample of the Fungus Sepedonium chrysospermum
A new cyclic pentapeptide, chrysosporide (1), was isolated from a New Zealand sample of the mycoparasitic fungus Sepedonium chrysospermum by bioactivity-guided fractionation. The planar structure was deduced by detailed spectroscopic analysis, and the absolute configurations of the amino acid residu...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2006-10, Vol.69 (10), p.1481-1484 |
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| container_issue | 10 |
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| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 69 |
| creator | Mitova, Maya I Stuart, Blair G Cao, Grace H Blunt, John W Cole, Anthony L. J Munro, Murray H. G |
| description | A new cyclic pentapeptide, chrysosporide (1), was isolated from a New Zealand sample of the mycoparasitic fungus Sepedonium chrysospermum by bioactivity-guided fractionation. The planar structure was deduced by detailed spectroscopic analysis, and the absolute configurations of the amino acid residues were defined by Marfey's method. As both enantiomers of Leu occurred in chrysosporide, molecular mechanics calculations were applied to the analysis to distinguish between the possible structural isomers. Only the lowest energy conformers of the cyclo-(l -Val-d-Ala-l-Leu-l-Leu-d-Leu) isomer were in agreement with the observed NOEs, suggesting that this was the most probable amino acid sequence for chrysosporide (1). |
| doi_str_mv | 10.1021/np060137o |
| format | Article |
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Only the lowest energy conformers of the cyclo-(l -Val-d-Ala-l-Leu-l-Leu-d-Leu) isomer were in agreement with the observed NOEs, suggesting that this was the most probable amino acid sequence for chrysosporide (1).</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np060137o</identifier><identifier>PMID: 17067166</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Amino Acid Sequence ; Aminoacids, peptides. Hormones. Neuropeptides ; Analytical, structural and metabolic biochemistry ; Animals ; Ascomycota - chemistry ; Biological and medical sciences ; Crystallography, X-Ray ; Drug Screening Assays, Antitumor ; Fundamental and applied biological sciences. 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| ispartof | Journal of natural products (Washington, D.C.), 2006-10, Vol.69 (10), p.1481-1484 |
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| subjects | Amino Acid Sequence Aminoacids, peptides. Hormones. Neuropeptides Analytical, structural and metabolic biochemistry Animals Ascomycota - chemistry Biological and medical sciences Crystallography, X-Ray Drug Screening Assays, Antitumor Fundamental and applied biological sciences. Psychology Leukemia P388 Mice Models, Chemical Molecular Structure New Zealand Peptides, Cyclic - chemistry Peptides, Cyclic - isolation & purification Peptides, Cyclic - pharmacology Protein Conformation Proteins Stereoisomerism |
| title | Chrysosporide, a Cyclic Pentapeptide from a New Zealand Sample of the Fungus Sepedonium chrysospermum |
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