5-Isothiocyanato-1-naphthalene azide and rho-azidophenylisothiocyanate. Synthesis and application in hydrophobic heterobifunctional photoactive cross-linking of membrane proteins.
Two hydrophobic, heterobifunctional azidoarylisothiocyanates have been synthesized. The reagents are applicable for group-directed modification of membrane-integrated protein segments and subsequent photo-induced cross-linking with neighbouring membrane constituents. Both 5-isothiocyanato-1-naphthalene azide and p-azidophenylisothiocyanate are chemically characterized with respect to structure and photosensitivity. The reagents compete for the documented phenylisothiocyanate binding site(s) in bacteriorhodopsin and to the anion-exchange protein (band 3) of human erythrocytes. Photoactivation of azidoarylisothiocyanate-labeled membrane proteins leads to homopolymers when cross-linked in purple membranes or in vesicles enriched in the anion-exchange protein.
D001457:Anion Exchange Protein 1, Erythrocyte; D001386:Azides / Q000138:chemical synthesis*; D001436:Bacteriorhodopsins / Q000032:analysis; D001798:Blood Proteins / Q000032:analysis; D003432:Cross-Linking Reagents / Q000138:chemical synthesis*; D017879:Isothiocyanates; D008565:Membrane Proteins; D010777:Photochemistry
D001457:Anion Exchange Protein 1, Erythrocyte; D001386:Azides; D001798:Blood Proteins; D003432:Cross-Linking Reagents; D017879:Isothiocyanates; D008565:Membrane Proteins; D001436:Bacteriorhodopsins; C035136:4-azidophenylisothiocyanate; C035137:5-isothiocyanato-1-naphthalene azide