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Synthesis and characterization of amino protected peptides derived from amino-α- hydroxyiminophosphonates

✍ Scribed by Eli Breuer; Muhammad Safadi; Michael Chorev; Adam Vineze; Peter Bel


Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
408 KB
Volume
47
Category
Article
ISSN
0040-4020

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✦ Synopsis


Diisopropyl 2-amino-l-hydroxyiminoethylphosphonate (2_a), derived from glycine, and diisopropyl 4-amino-l-hydroxyiminobutylphosphonate (2__~), 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-l-hydroxyiminoethylphosphonate (3__a) and diisopropyl 4-(t-Boc-L-Phe)amino-l-hydroxyiminobutylphosphonate (3__~). Diisopropyl 3-amino-1--hydroxyiminopropylphosphonate (L~), derived from #-Ala, and diisopropyl 2-amino-l-hydroxyiminopropylphosphonate (Ld_), derived from DL-AIa, were reacted with Boc-DL--Ala-OH by the mixed anhydride method to give peptide analogs diisopropyl 3-(t-Boc--L-Ala)amino-l-hydroxyiminopropylphosphonate (4__b) an¢ di~opropyl 2-(t-Boc-L-Ala)amino--l-hydroxyiminopropylphosphonate (4d) respectively. H, P NMR and FAB Mass spectra of the peptide analogs are reported.


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