Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil

doi:10.1007/s13659-022-00348-x

Natural Products and Bioprospecting ›› 2022, Vol. 12 ›› Issue (4): 26-26.DOI: 10.1007/s13659-022-00348-x

• Original Article • Previous Articles Next Articles

Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil

Guidmar C. Donalle^1,2, María Martha Martorell³, Gastón E. Siless^1,2, Lucas Ruberto³, Gabriela M. Cabrera^1,2

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

Received:2022-04-19 Online:2022-08-12 Published:2022-08-24
Contact: Lucas Ruberto,E-mail:luruberto@gmail.com;Gabriela M.Cabrera,E-mail:gabyc@qo.fcen.uba.ar
Supported by:
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.

Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil

Guidmar C. Donalle^1,2, María Martha Martorell³, Gastón E. Siless^1,2, Lucas Ruberto³, Gabriela M. Cabrera^1,2

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

通讯作者: Lucas Ruberto,E-mail:luruberto@gmail.com;Gabriela M.Cabrera,E-mail:gabyc@qo.fcen.uba.ar
基金资助:
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.

Abstract

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.

Key words: Cyclic peptide, Cadophora malorum, Metal binding

摘要： 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.

关键词: Cyclic peptide, Cadophora malorum, Metal binding

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[J]. Natural Products and Bioprospecting, 2022, 12(4): 26-26.

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Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil

Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil

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