SYNTHESIS AND CHARACTERIZATION OF AMINO PROTECTED PEPTIDES DERIVED FROM AMINO-ALPHA-HYDROXYIMINOPHOSPHONATES

Diisopropyl 2-amino-1-hydroxyiminoethylphosphonate (2a), derived from glycine, and diisopropyl 4-amino-1-hydroxyiminobutylphosphonate (2c), derived from GABA, were reacted with Boc-L-Phe-OH by the mixed anhydride method to yield novel peptide analogs diisopropyl 2-(t-Boc-L-Phe) amino-1-hydroxyiminoethylphosphonate (3a) and diisopropyl 4-(t-Boc-L-Phe) amino-1-hydroxyiminobutylphosphonate (3c). Diisopropyl 3-amino-1-hydroxyiminopropylphosphonate (2b), derived from beta-Ala, and diisopropyl 2-amino-1-hydroxyiminopropylphosphonate (2d), derived from DL-Ala, were reacted with Boc-DL-Ala-OH by the mixed anhydride method to give peptide analogs diisopropyl 3-(t-Boc-L-Ala) amino-1-hydroxyiminopropylphosphonate (4b) and diisopropyl 2-(t-Boc-L-Ala) amino-1-hydroxyiminopropylphosphonate (4d) respectively. H-1, P-31 NMR and FAB Mass spectra of the peptide analogs are reported.