956515-39-2Relevant academic research and scientific papers
Design and synthesis of a tag-free chemical probe for photoaffinity labeling
Mayer, Timo,Maier, Martin E.
, p. 4711 - 4720 (2007)
The novel aromatic diazirine-containing benzoic acid 22 was prepared via the diazirine 11 as the key intermediate. After formylation of the aryl ring and cleavage of the methyl ether function of aldehyde 12, the phenolic hydroxy group was converted into the ether 21 terminating in an alkyne function. Oxidation of the aldehyde to the carboxylic acid provided the chemical probe 22 designed for tag-free photoaffinity labeling. In a proof-of-concept study it could be shown that irradiation of the simple ester 23 indeed yields the methanol insertion product 24. A subsequent click reaction with benzyl azide 20 led to the triazole 25. A more complicated example was realized with the esterification of bafilomycin A1 (27) with acid 22. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
