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Título: | Conversion of "customizable Units" into N-Alkyl Amino Acids and Generation of N-Alkyl Peptides |
Autor: | Saavedra, Carlos J. CSIC ORCID; Carro, Carmen; Hernández, Dácil CSIC ORCID ; Boto, Alicia CSIC ORCID | Palabras clave: | Amino acids Peptides Hdroxyproline |
Fecha de publicación: | 23-may-2019 | Editor: | ACS Publications | Citación: | Journal of Organic Chemistry 84 (13): 8392-8410 (2019) | Resumen: | An efficient conversion of hydroxyproline >customizable> units into new amino acids with a variety of N-alkyl substituents is described. The process is versatile and can afford valuable N-methyl amino acids and N,O-acetals. In addition, it allows the introduction of N-homoallylic substituents and N-chains with terminal ester, ketone, or cyano groups. These chains could be used for peptide extension or conjugation to other molecules (e.g., by olefin metathesis, peptide ligation, etc.). The transformation is carried out in just two (for R = CHOAc) or three steps (scission of the pyrrolidine ring, manipulation of the α-chain, and the N-substituent) under mild, metal-free conditions, affording products with high optical purity. | Versión del editor: | https://doi.org/10.1021/acs.joc.9b00114 | URI: | http://hdl.handle.net/10261/188316 | DOI: | 10.1021/acs.joc.9b00114 | Identificadores: | doi: 10.1021/acs.joc.9b00114 e-issn: 1520-6904 issn: 0022-3263 |
Aparece en las colecciones: | (IPNA) Artículos |
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Conversion_of_“Customizable_Units”_into_N‑Alkyl_Amino_Acids_and_Generation_of_N‑Alkyl_Peptides.pdf | 2,19 MB | Adobe PDF | Visualizar/Abrir |
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