Título:
Thioester deprotection using a biomimetic NCL approach
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Autor:
Villamil, Valentina
Saiz, Cecilia
Mahler, Graciela
Saiz, Cecilia
Mahler, Graciela
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Tipo de documento:
Artículo
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TIOL
TIOESTER
ESTERIFICACION
TRANSESTERIFICACION
LIGADURA QUIMICA NATIVA
TIOESTER
ESTERIFICACION
TRANSESTERIFICACION
LIGADURA QUIMICA NATIVA
Año de publicación:
2022
Contenido:
Resumen:
The reversibility of the thiol-thioester linkage has been broadly employed in many fields of biochemistry (lipid synthesis) and chemistry (dynamic combinatorial chemistry and material science). When the transthioesterification is followed by a S-to-N acyl transfer to give an amide bond, it is called Native Chemical Ligation (NCL), a high-yield chemoselective process used for peptide synthesis. Recently, we described thioglycolic acid (TGA) as a useful reagent for thioester deprotection both in solution and anchored to a solid-support under mild conditions. Inspired by NCL, in this work, we extended this approach and explored the use of 2-aminothiols for the deprotection of thiols bearing an acyl group. The best results were obtained using cysteamine or L-cysteine in an aqueous buffer pH 8 at room temperature for 30 min. The described approach was useful for S-acetyl, S-butyryl, and S-benzoyl heterocycles deprotection with yields up to 84%. Employing this methodology, we prepared six new analogs 2 of mercaptomethyl bisthiazolidine 1, a useful inhibitor of a wide-range of Metallo-β-Lactamases (MBLs). Compared with the previous methodologies (TGA polymer supported and TGA in solution), the biomimetic deprotection herein described presents better performance with higher yields, shorter reaction times, less time-consuming operations, easier setup, and lower costs.
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Frontiers Media
EN:
Frontiers in Chemistry v.10, 2022.-- e934376.
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Citación:
Villamil, V, Saiz, C y Mahler, G. "Thioester deprotection using a biomimetic NCL approach". Frontiers in Chemistry v.10. [en línea] 2022, vol. 10, e934376. DOI: 10.3389/fchem.2022.934376
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Licencia Creative Commons Atribución (CC - By 4.0)
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| Ficheros | Descripción | Tamaño | Formato | ||
|---|---|---|---|---|---|
| AA Villamil, Valentina et al. Frontiers in chemistry, 2022. --.pdf | — | 2.23 MB | Adobe PDF |