Photoswitchable dipeptides comprised of azobenzene and amino acid substituents provide details about the microenvironment of assembled structures and photoactivated molecular changes. We have synthesized ortho-fluorine containing derivatives of phenylazobenzyloxycarbonyl(pz)-Pro-Leu (Pz-Pro-Leu) conjugates. It is known that solvent polarity can affect azobenzene photoisomerization but the literature contains little information on the effect of amino acid substituents. Chambers and Hayworth reported an unexpected stabilization of the cis azobenzene isomer in aqueous solution for Pz-didpeptide. We have prepared similar azobenzene dipeptide and bioconjugates conjugates to study this effect more closely. We have introduced ortho-fluorine substituents to facilitate diagnosis via 19F NMR. 19F NMR is a powerful tool for studies of aggregation, protein folding, and microenvironment characteristics. We will report solution phase synthesis of ortho-fluorine conjugates of Pz-dipeptides and characterization.

Synthesis of ortho-fluorine derivatives of phenylazobenzyloxycarbonyl(pz)-Pro-Leu for photodynamic study

249th National Meeting (2015)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.