Portal de Periódicos da CAPES

Conversion of “Customizable Units” into N -Alkyl Amino Acids and Generation of N -Alkyl Peptides

2019; American Chemical Society; Volume: 84; Issue: 13 Linguagem: Inglês

10.1021/acs.joc.9b00114

1520-6904

Carlos J. Saavedra, Carmen Carro, Dácil Hernández, Alicia Boto,

Peptidase Inhibition and Analysis

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 = CH2OAc) 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.