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Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil |
| Guidmar C. Donalle1,2, María Martha Martorell3, Gastón E. Siless1,2, Lucas Ruberto3, Gabriela M. Cabrera1,2 |
1. Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Universidad de Buenos Aires, Buenos Aires, Argentina;
2. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (UMYMFOR), CONICET-Universidad de Buenos Aires, Buenos Aires, Argentina;
3. Instituto Antártico Argentino, Instituto Nanobiotec, CONICET-Universidad de Buenos Aires, Buenos Aires, Argentina |
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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.
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| Keywords
Cyclic peptide
Cadophora malorum
Metal binding
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| Fund:The authors thank Universidad de Buenos Aires[UBACYT 2018-100246, PDE-48-2020], CONICET[PIP 112 20200101898] and ANPCyT[PICT 2018-0930, PICT E 2018-0031] for partial financial support. |
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Corresponding Authors:
Lucas Ruberto,E-mail:luruberto@gmail.com;Gabriela M.Cabrera,E-mail:gabyc@qo.fcen.uba.ar
E-mail: luruberto@gmail.com;gabyc@qo.fcen.uba.ar
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Issue Date: 12 August 2022
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