Fluorous aryldiazirine photoaffinity labeling reagents.
Two fluorous versions of trifluoromethyldiazirine derivatives have been designed and synthesized. The new photoaffinity labeling reagents have reactivity similar to that of their aryltrifluoromethyldiazirine parent when activated in MeOH, while the reaction products can be efficiently separated over fluorous silica gel. The alcohol group in the two reagents is further converted to activated carboxylic acid and amine, which enable coupling both reagents with small molecules and macromolecules under mild conditions.
Song
Zhiquan
Z
Division of Medicinal Chemistry and Natural Products, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, USA.
Zhang
Qisheng
Q
D000588:Amines / Q000737:chemistry; D001389:Azirines / Q000138:chemical synthesis* / Q000737:chemistry; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003978:Diazomethane / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D019920:Photoaffinity Labels / Q000138:chemical synthesis* / Q000737:chemistry
D000588:Amines; D001389:Azirines; D001555:Benzene Derivatives; D006845:Hydrocarbons, Fluorinated; D007202:Indicators and Reagents; D019920:Photoaffinity Labels; D003978:Diazomethane