Abstract:
The utility of unnatural amino acids has been extensively explored in the construction of
new building blocks, molecular scaffolds, and therapeutic leads. For instance, highly
versatile g-amino -keto acids present in several biologically active peptides, has been
used as precursor for the synthesis of many biologically relevant molecules such as
statines, ketomethylene dipeptide isosteres, -lactams, tricarbonyl compounds,
rhodopeptins, substituted pyridines, fluorescent amino acid tags, cholecystokinin
receptor antagonists,
g-amino , -unsaturated esters, and -azo -carbonyl
compounds. Here we are demonstrating the utility of -keto-g-amino ester in the
synthesis of highly symmetrical tetrasubstituted pyrazines through simple aerial
oxidation. In addition we also exploited this mild and biocompatible protocol for the selfstapling
of peptides. The easy synthesis, mild and biocompatible aromatization of the -
keto-g-amino esters and peptide -keto-esters may find application in biological and
medicinal chemistry as well as in material science.
