title: Cyclopropenone-caged Sondheimer diyne (dibenzo[a,e]cyclooctadiyne): a photoactivatable linchpin for efficient SPAAC crosslinking.
abstract: The first fully conjugated bis-cyclopropenone (photo-DIBOD), a derivative of dibenzo[a,e][8]annulene, has been synthesized. 350-420 nm irradiation of this robust compound results in the efficient formation of dibenzo [a,e] cyclooctadiyne, an unstable, but useful SPAAC cross-linking reagent. Since photo-DIBO doesn't react with organic azides, this method allows for the spatiotemporal control of the ligation of two azide-tagged substrates.
authors.affiliation: Department of Chemistry, University of Georgia, Athens, GA 30602, USA. vpopik@uga.edu.
authors.forename: Dewey A
authors.initials: DA
authors.lastname: Sutton
authors.forename: Seok-Ho
authors.initials: SH
authors.lastname: Yu
authors.forename: Richard
authors.initials: R
authors.lastname: Steet
authors.forename: Vladimir V
authors.initials: VV
authors.lastname: Popik
mesh_terms: D015153:Blotting, Western; D003432:Cross-Linking Reagents / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D053280:Diynes / Q000737:chemistry*; D004591:Electrophoresis, Polyacrylamide Gel; D008027:Light; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000737:chemistry*; D012235:Rhodamines / Q000737:chemistry
chemical_list: D003432:Cross-Linking Reagents; D003521:Cyclopropanes; D053280:Diynes; D011083:Polycyclic Compounds; D012235:Rhodamines; C120343:cyclopropenone; C000611763:dibenzo(a,e)cyclooctadiyne; C029773:rhodamine B