PEPTIDE DERIVATIVES OF PHOSPHONIC AND PHOSPHINIC ACIDS

摘要

1533240 Phosphorous containing peptides ROCHE PRODUCTS Ltd 26 Jan 1976 [27 Jan 1975 20 Nov 1975] 15434/78 and 15435/78 Divided out of 1533239 Heading C3H [Also in Division C2] The invention comprises compounds of Formula I and salts thereof wherein n is 1, 2 or 3; R10 is H or a C 1-6 alkyl, C 3-6 cycloalkyl, (C 3-6 cycloalkyl)-(C 1-6 alkyl), aryl, or aryl-(C 1-6 alkyl) group said groups being optionally substituted by one or more amino, hydroxy, mercapto, methylthio, carboxy, or guanidino groups so as to form the characterizing residue of an L-α-amino acid of the type found in proteins; and any "aryl" moiety optionally being substituted by hydroxy, halogen nitro, C 1-6 alkyl or C 1-6 alkoxy; each R20 (independently) and R30 is the characterizing residue of an L-α-amino acid or of the type found in proteins; R30' is H; or R30 and R30' together form the characterizing residue of an L-α-amino acid of the type found in proteins; any amino or other functional groups present in R10, R20, R30 and R30' optionally being in protected form; R40 is Me or R41; R41 is OH or a C 1-6 alkoxy protecting group; R5 is H or a protecting group; with the proviso that at least one of R10, R20, R30, R40, R41 and R5 is a protecting group or is in protected form. When asymmetric the configuration at * is L and at ** is R. Preparation of I is by conventional synthesis of any of the peptide linkages in the molecule. In a modification, a starting material having mixed configuration at ** is used, and the resulting (RS) isomer mixture separated, e.g. by crystallization, chromatography, or fractional crystallization with a base, e.g.α-methylbenzylamine to give the desired R isomer.