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Chemical Process for the selective modification of peptides

Other TitlesProceso químico para la modificación selectiva de péptidos
AuthorsBoto, Alicia ; Hernández, Rosendo ; Saavedra, Carlos Javier ; Álvarez, Eleuterio
Issue Date3-Jan-2013
CitationWO2013001120 A1
Abstract[EN] Method for selective modification of a peptide of general formula (30) to obtain a peptide of general formula (31) where [aa]n represents the N-terminal end of the peptide with a variable number n of amino acids, [aa]m represents the C-terminal end with a variable number m of amino acids, and the sum of m + n is an integer between 1 and 50, Y is chosen from -CH2-, -CH(alkyl)- and -C(=0)-, Z is chosen from hydrogen or an amine-protecting group, and [A] is chosen from groups in which A represents CH2, a substituted carbon or a heteroatom, and i represents an integer between 1 and 10; characterized in that said method comprises the steps of [a] oxidative radical cleavage of the peptide of general formula (30), and [b] addition of a carbon nucleophile to the imine intermediate formed in order to obtain a peptide of general formula (31). The invention also relates to the peptides of formula (31) obtained by means of this method and peptides derived therefrom.
[ES] Procedimiento de modificación selectiva de un péptido de fórmula general (30) para obtener un péptido de fórmula general (31) donde [aa]n representa el extremo N-terminal del péptido con un número variable n de aminoácidos, [aa]m represeta el extremo C-terminal con un número variable m de amino ácidos, y la suma de m+n es un valor entero entre 1 y 50, Y se elige entre -CH2-, -CH(alquilo)- y -C(=0)-, Z se elige entre hidrógeno o un grupo protector de amina, y [A] se elige entre grupos donde A representa CH2, un carbono sustituido o un heteroátomo, e i representa un valor entre 1 y 10; caracterizado porque dicho procedimiento comprende las etapas de [a] escisión radicalaria oxidativa del péptido de fórmula general (31). Así como los péptidos de fórmula (31) obtenidos por este procedimiento y péptidos derivados de éstos.
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