Exploratory photochemistry of fluorinated aryl azides. Implications for the design of photoaffinity labeling reagents.
AuthorsSchnapp KA, Poe R, Leyva E, Soundararajan N, Platz MS
JournalBioconjug Chem
PubMed ID7873649
'A series of fluorinated aryl azides and fluorinated azidobenzoates were studied by laser flash photolysis techniques. Using the pyridine ylide probe method it was possible to determine whether a singlet nitrene or ring-expanded ketenimine ylide is the trappable intermediate that is generated at ambient temperature. It was determined that two ... More
Preservation of immunoreactivity in the photolabeling of the B72.3 human antibody.
AuthorsPandurangl RS, Karra SR, Kuntz RR, Volkert WA
JournalPhotochem Photobiol
PubMed ID8787004
'A versatile photochemical method of labeling human antibodies is described. Labeling is achieved by photolyzing 4-azido-2,3,5,6-tetrafluoro-14C-methylbenzoate and the B72.3 human antibody in a buffer at physiological pH. The photochemically produced nitrene presumably inserts into bonds in the hydrophobic part of the antibody resulting in > 75% attachment of the photoprobe. ... More
A laser flash photolysis study of di-, tri- and tetrafluorinated phenylnitrenes; implications for photoaffinity labeling.
AuthorsSchnapp KA, Platz MS
JournalBioconjug Chem
PubMed ID7873650
Several fluorinated aryl azides (2,6 and 2,4-difluorophenyl azide, 2,4,6-triflurorophenyl azide, and methyl 4-azido-2,3,5,6-tetrafluorobenzoate) were studied by laser flash photolysis techniques. In each case, the azides from singlet nitrenes which can be intercepted with pyridine to form ylides. This allowed determination of the rate constant for ring expansion of the singlet ... More