Synthesis of meso-tetraarylporphyrins possessing amino and carboxy groups and their peptides

Abstract

meso-Tris(3,5-di-tert-butylphenyl)porphyrin (P- H ) is bonded with L-phenylalanine (H-Phe-OH) directly at the unsubstituted meso-position of the former and the p-position of phenyl group of the latter to afford chiral porphyrin-amino acid conjugate H-Phe(p-P)-OH. The N-(9-fluorenyl)-methyloxycarbonyl compound, Fmoc-Phe(p-P)-OH, was synthesized without any loss of enantiomeric purity (based on chiral HPLC analysis) from commercially available L-tyrosine and was useful for preparation of the peptides in both liquid and solid phases. Other meso-tetraarylporphyrins possessing multi-amino acid moieties are reported, as well as achiral porphyrin-amino acids readily prepared and their dipeptidyl porphyrin dyads.