Dehydrooligopeptides. III. Synthesis of (Z,Z)- and (Z,E)-Geometric Isomers of Dehydrodipeptides and Their Base-catalyzed Transformation to the Hydantoin Derivatives

Article abstract of DOI:10.1246/bcsj.55.2147

N-Benzyloxycarbonyl (Cbz)-(Z,E)-dehydrodipeptides, comprised of both (Z)- and (E)-α-dehydroamino acid residues, were first synthesized by dehydrochlorination of Cbz-(Z)-dehydrodipeptides containing an erythro-3-chloro-2-aminobutanoate moiety.Base-catalyzed transformation of the individual Cbz-(Z, Z)- and (Z, E)-dehydrodipeptides was carried out to give the corresponding new hydantoin derivatives.The NMR spectroscopic differences between the geometric isomers of both dehydrodipeptides and their hydantoin derivatives were elucidated.