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Open AccessArticle

Structural Elucidation of Antibiotic TKR2999, an Antifungal Lipodepsipeptide Isolated from the Fungus Foliophoma fallens

Fundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avenida del Conocimiento 34, Parque Tecnológico de Ciencias de la Salud, E-18016 Granada, Spain
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Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Antibiotics 2020, 9(6), 278; https://doi.org/10.3390/antibiotics9060278
Received: 29 April 2020 / Revised: 22 May 2020 / Accepted: 23 May 2020 / Published: 26 May 2020
An antifungal lipodepsipeptide was obtained from cultures of the fungus Foliophoma fallens CF-236885. Its structure, elucidated by HRMS and NMR spectroscopy, contained Gly, Thr, Asn, β-Ala, Orn, Ala, two Ser residues, and 3-hydroxy-4-methylhexadecanoic acid. The absolute configuration of its amino acid residues was determined using Marfey’s analysis and J-based configuration analysis helped to establish the relative configuration of the 3-hydroxy-4-methylhexadecanoic acid moiety. A literature search retrieved a patent describing antibiotic TKR2999 (1), whose non-disclosed structure was confirmed to be identical to that found for our compound, according to its physicochemical properties and NMR spectra. Compound 1 displayed potent antifungal activity against Aspergillus fumigatus and a panel of Candida strains. View Full-Text
Keywords: Foliophoma fallens; antibiotic TKR2999; lipodepsipeptide; structural elucidation; Marfey’s analysis; antifungal activity Foliophoma fallens; antibiotic TKR2999; lipodepsipeptide; structural elucidation; Marfey’s analysis; antifungal activity
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MDPI and ACS Style

Crespo, G.; Pérez-Victoria, I.; Ortiz-López, F.J.; González-Menéndez, V.; de la Cruz, M.; Cautain, B.; Sánchez, P.; Vicente, F.; Genilloud, O.; Reyes, F. Structural Elucidation of Antibiotic TKR2999, an Antifungal Lipodepsipeptide Isolated from the Fungus Foliophoma fallens. Antibiotics 2020, 9, 278. https://doi.org/10.3390/antibiotics9060278

AMA Style

Crespo G, Pérez-Victoria I, Ortiz-López FJ, González-Menéndez V, de la Cruz M, Cautain B, Sánchez P, Vicente F, Genilloud O, Reyes F. Structural Elucidation of Antibiotic TKR2999, an Antifungal Lipodepsipeptide Isolated from the Fungus Foliophoma fallens. Antibiotics. 2020; 9(6):278. https://doi.org/10.3390/antibiotics9060278

Chicago/Turabian Style

Crespo, Gloria; Pérez-Victoria, Ignacio; Ortiz-López, Francisco J.; González-Menéndez, Víctor; de la Cruz, Mercedes; Cautain, Bastien; Sánchez, Pilar; Vicente, Francisca; Genilloud, Olga; Reyes, Fernando. 2020. "Structural Elucidation of Antibiotic TKR2999, an Antifungal Lipodepsipeptide Isolated from the Fungus Foliophoma fallens" Antibiotics 9, no. 6: 278. https://doi.org/10.3390/antibiotics9060278

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