Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil
Abstract The Antarctic fungus Cadophora malorum produces previously undescribed cyclic heptapeptides (cadophorin A and B) containing an anthranilic acid residue. The planar structure of these peptides was determined by high-resolution mass spectrometry combined with extensive 1D and 2D NMR spectrosc...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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SpringerOpen
2022-07-01
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| Series: | Natural Products and Bioprospecting |
| Subjects: | |
| Online Access: | https://doi.org/10.1007/s13659-022-00348-x |
| _version_ | 1811293541223104512 |
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| author | Guidmar C. Donalle María Martha Martorell Gastón E. Siless Lucas Ruberto Gabriela M. Cabrera |
| author_facet | Guidmar C. Donalle María Martha Martorell Gastón E. Siless Lucas Ruberto Gabriela M. Cabrera |
| author_sort | Guidmar C. Donalle |
| collection | DOAJ |
| description | Abstract The Antarctic fungus Cadophora malorum produces previously undescribed cyclic heptapeptides (cadophorin A and B) containing an anthranilic acid residue. The planar structure of these peptides was determined by high-resolution mass spectrometry combined with extensive 1D and 2D NMR spectroscopy. The absolute configuration of the amino acids was determined by Marfey’s method, with HPLC analysis of FDVA (Nα-(2,4-dinitro-5-fluorphenyl)-l-valinamide) derivatives making use of a PFP column. Remarkably, cadophorin 2 possesses both the uncommon d-Ile and d-allo-Ile in its structure. The peptides have metal binding properties as shown by LCMS with post column addition of metal salt solutions. These results were supported by DFT calculations. Graphical Abstract |
| first_indexed | 2024-04-13T05:02:54Z |
| format | Article |
| id | doaj.art-a4f73dc546944d0b89984a23cdbfee29 |
| institution | Directory Open Access Journal |
| issn | 2192-2195 2192-2209 |
| language | English |
| last_indexed | 2024-04-13T05:02:54Z |
| publishDate | 2022-07-01 |
| publisher | SpringerOpen |
| record_format | Article |
| series | Natural Products and Bioprospecting |
| spelling | doaj.art-a4f73dc546944d0b89984a23cdbfee292022-12-22T03:01:17ZengSpringerOpenNatural Products and Bioprospecting2192-21952192-22092022-07-0112111010.1007/s13659-022-00348-xCyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soilGuidmar C. Donalle0María Martha Martorell1Gastón E. Siless2Lucas Ruberto3Gabriela M. Cabrera4Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Universidad de Buenos AiresInstituto Antártico Argentino, Instituto Nanobiotec, CONICET-Universidad de Buenos AiresFacultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Universidad de Buenos AiresInstituto Antártico Argentino, Instituto Nanobiotec, CONICET-Universidad de Buenos AiresFacultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Universidad de Buenos AiresAbstract The Antarctic fungus Cadophora malorum produces previously undescribed cyclic heptapeptides (cadophorin A and B) containing an anthranilic acid residue. The planar structure of these peptides was determined by high-resolution mass spectrometry combined with extensive 1D and 2D NMR spectroscopy. The absolute configuration of the amino acids was determined by Marfey’s method, with HPLC analysis of FDVA (Nα-(2,4-dinitro-5-fluorphenyl)-l-valinamide) derivatives making use of a PFP column. Remarkably, cadophorin 2 possesses both the uncommon d-Ile and d-allo-Ile in its structure. The peptides have metal binding properties as shown by LCMS with post column addition of metal salt solutions. These results were supported by DFT calculations. Graphical Abstracthttps://doi.org/10.1007/s13659-022-00348-xCyclic peptideCadophora malorumMetal binding |
| spellingShingle | Guidmar C. Donalle María Martha Martorell Gastón E. Siless Lucas Ruberto Gabriela M. Cabrera Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil Natural Products and Bioprospecting Cyclic peptide Cadophora malorum Metal binding |
| title | Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil |
| title_full | Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil |
| title_fullStr | Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil |
| title_full_unstemmed | Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil |
| title_short | Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil |
| title_sort | cyclic heptapeptides with metal binding properties isolated from the fungus cadophora malorum from antarctic soil |
| topic | Cyclic peptide Cadophora malorum Metal binding |
| url | https://doi.org/10.1007/s13659-022-00348-x |
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