Cyclic peptides. XIII. Asymmetric synthesis of aromatic L-alpha-amino acids through hydrogenation of cyclic dehydrodipeptides.
Four cyclic dehydrodipeptides, cyclo (-delta aminoacyl-L-Ala-), in which aminoacyl is Phe, Apb (2-amino-4-phenylbutanoic acid), App (2-amino-5-phenylpentanoic acid) and Aph (2-amino-6-phenylhexanoic acid), were prepared by condensation of cyclo (-N-Ac-Gly-N-Ac-L-Ala-) with the corresponding aldehydes. Among them, the yield of cyclo (-delta Apb-L-Ala-) was exceptionally low. Each compound was hydrogenated in the presence of Pd black at various temperatures and chiral induction in hydrogenation was evaluated. Low chiral induction at high temperature (50 degrees) was observed in the case of cyclo (-delta Phe-L-Ala-). Optically pure L-Apb, L-App and L-Aph were obtained from the corresponding cyclic dehydrodipeptides, respectively, by hydrogenation and subsequent acid hydrolysis.
D000596:Amino Acids; D010084:Oxidation-Reduction; D010456:Peptides, Cyclic / Q000138:chemical synthesis
D000596:Amino Acids; D010456:Peptides, Cyclic