Abstract:
:A novel radioisotope-free photo-affinity probe containing the 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group was designed and synthesized. This very compact functionality is envisaged to allow photochemically-induced coupling of a compound to its target followed by click reaction coupling with an azido-biotin reagent in order to facilitate purification of the labeled target. In a proof-of-concept study we have shown that 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group could be photolyzed to efficiently furnish the methanol adduct 23 and that the generated highly unstable carbene does not react with the neighboring acetylene moiety. A subsequent click reaction with the azido-biotin derivative 25 proceeded smoothly to give triazole 26. This chemical probe should thus be of unique value for facilitating identification of the molecular structure of the target of a bioactive compound.
journal_name
Bioorg Med Chemjournal_title
Bioorganic & medicinal chemistryauthors
Kumar NS,Young RNdoi
10.1016/j.bmc.2009.06.048subject
Has Abstractpub_date
2009-08-01 00:00:00pages
5388-95issue
15eissn
0968-0896issn
1464-3391pii
S0968-0896(09)00611-7journal_volume
17pub_type
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