Asymmetric Synthesis Utilizing Oxazolidinone-Fused Aziridines

Incorporation of unnatural amino acids(UAAs) or fluorinated amino acids at specific sites in the proteome has become a powerful tool to investigate, engineerprotein structure and study function of enzymes, peptides and proteins. In addition, fluorinated amino acids has their potential as probes in PET and NMR for studying the behavior of enzymes and for incorporation into peptide structures and drug candidates. Therefore, synthesis of these unnatural amino acids(UAAs) has received much attention. In this proposal, we plan to utilize the regio- and diastereo-selective ring-opening of the 2-oxazolidinone fused aziridine (3-oxa-1-azabicyclo[3.1.0]hexan-2-one) to achieve this goal. Various aziridines are designed, synthesized and applied as the key intermediates to prepare unnatural amino acids. Further application to syntheses of natural products or biologically active molecules is also possible.