Título:
Synthesis of cyclotetrapeptides analogues to natural products as herbicides
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Autor:
Irabuena, Camila
Posada, Laura
Rey, Luciana
Scarone, Laura
Davyt, Danilo
Villalba, Juana
Serra, Gloria
Posada, Laura
Rey, Luciana
Scarone, Laura
Davyt, Danilo
Villalba, Juana
Serra, Gloria
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Tipo de documento:
Artículo
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QUIMICA ORGANICA
CICLOPEPTIDOS
PEPTIDOS
HERBICIDAS
CICLOPEPTIDOS
PEPTIDOS
HERBICIDAS
Año de publicación:
2022
Contenido:
Resumen:
The synthesis of cyclotetrapeptides analogues of the natural products tentoxin and versicotide D was achieved in good yield by solid phase peptide synthesis (SPPS) of their linear precursors and solution phase cyclization. All the cyclopeptides and several open precursors were evaluated as herbicides. Five cyclopeptides and five lineal peptides showed a significant inhibition (>70%) of Ryegrass seed’s radicle growth at 67 μg/mL. The evaluation at lower concentrations (4–11 μM) indicates two cyclopeptides analogs of tentoxin, which present one (N-Methyl-D-Phe), and two N-MeAA (N-Methyl-Ala and N-Methyl-Phe), respectively, as the most active of them, showing remarkable phytotoxic activity. In two cases, the open precursors are as active as their corresponding cyclopeptide. However, many linear peptides are inactive and their cyclization derivatives showed herbicidal activ-
ity. In addition, two cyclopeptide analogues of versicotide D showed more improved activity than the natural product. The results indicate that the peptide sequence, the amino acid stereochemistry and the presence of N-methyl group have important influence on the phytotoxic activity. Moreover, several compounds could be considered as lead candidates in the development of bioherbicides.
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MDPI
EN:
Molecules, v.27, n° 21, 2022. -- e7350
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Citación:
Irabuena, C, Posada, L, Rey, L, y otros. "Synthesis of cyclotetrapeptides analogues to natural products as herbicides". Molecules. [en línea] 2022 vol.27, n° 21, e7350. DOI: https://doi.org/10.3390/molecules27217350
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Licencia Creative Commons Atribución (CC - By 4.0)
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| Ficheros | Descripción | Tamaño | Formato | ||
|---|---|---|---|---|---|
| AA Irabuena, Camila et al. Molecules, v.27, 2022. --.pdf | — | 877.07 KB | Adobe PDF |