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Título: | Metal-Free, Site-Selective Peptide Modification by Conversion of “Customizable” Units into β-Substituted Dehydroamino Acids |
Autor: | Saavedra, Carlos Javier; Hernández, Dácil CSIC ORCID ; Boto, Alicia CSIC ORCID | Palabras clave: | Organic synthesis Sustainable chemistry Regioselectivity Peptides Chemoselectivity Domino reactions |
Fecha de publicación: | 12-ene-2018 | Editor: | Wiley-VCH | Citación: | Chemistry-A European Journal 24(3): 599-607 (2018) | Resumen: | Our site-selective modification of serine or threonine units in peptides allows the generation of β-substituted dehydroamino acids, which increase peptide resistance to hydrolysis and may improve their biological properties. Both the terminal and internal positions can be modified, and different customizable units can be activated separately. Remarkably, high Z selectivity is achieved, even at internal positions. The conversion involves a one-pot oxidative radical scission/phosphorylation process by using the low-toxicity (diacetoxyiodo)benzene/iodine system as the scission reagent. The resulting α-amino phosphonates undergo a Horner-Wadsworth-Emmons reaction to produce the dehydroamino acid derivatives (in a Z/E ratio of usually >98:2) under mild and metal-free conditions. | Versión del editor: | https://doi.org/10.1002/chem.201703758 | URI: | http://hdl.handle.net/10261/181449 | DOI: | 10.1002/chem.201703758 | Identificadores: | doi: 10.1002/chem.201703758 e-issn: 1521-3765 issn: 0947-6539 |
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