The synthesis of two peptide mimetics of RGD, alpha-Tfm-Arg-Gly-Asp-Phe-NH2 9 and alpha-Tfm-Arg-Gly-Asp- NH-(CH2)2-C6H5 13, is described. The precursor of alpha-Tfm-ornithine was obtained in two synthetic steps from 2-N-Cbz- 2-Tfm-hexanediacid-1-alkyl ester and introduced into the peptide chain by alpha-carboxy-group activation via oxazolone. The introduction of the guanidine residue led to the final peptides as mixtures of the two diastereomers. Configurationally pure peptides were obtained in good yields by RP-HPLC
Synthesis of RGD analogues containing α-Tfm-arginine as potential fibrinogen receptor antagonists
RONDANIN, Riccardo;
1998
Abstract
The synthesis of two peptide mimetics of RGD, alpha-Tfm-Arg-Gly-Asp-Phe-NH2 9 and alpha-Tfm-Arg-Gly-Asp- NH-(CH2)2-C6H5 13, is described. The precursor of alpha-Tfm-ornithine was obtained in two synthetic steps from 2-N-Cbz- 2-Tfm-hexanediacid-1-alkyl ester and introduced into the peptide chain by alpha-carboxy-group activation via oxazolone. The introduction of the guanidine residue led to the final peptides as mixtures of the two diastereomers. Configurationally pure peptides were obtained in good yields by RP-HPLCFile in questo prodotto:
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