205485-25-2Relevant academic research and scientific papers
CARBENE MASS TAGGING
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, (2020/12/07)
The disclosure relates to a diazirine precursor mass tag compound represented by structural formula (I). Also disclosed is a method for detecting analytes in a sample, comprising derivatizing the analytes with the compound of formula (I), and detecting th
Design and synthesis of a tag-free chemical probe for photoaffinity labeling
Mayer, Timo,Maier, Martin E.
, p. 4711 - 4720 (2008/03/13)
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.
Aryldiazirine-modified pyroglutamates: Photoaffinity labels for glutamate
Bentz, Emilie L.,Gibson, Hannah,Hudson, Clare,Moloney, Mark G.,Seldon, Debbie A.,Wearmouth, Edwina S.
, p. 247 - 250 (2007/10/03)
The synthesis of an aryldiazirine-modified pyroglutamate is reported for potential application as a photoaffinity label at glutamate receptors. Detailed 13C NMR and 19F NMR spectroscopic characterisation data for these trifluoromethy
A new cleavable carbene-generating reagent with 3-phenyl-3-trifluoromethyldiazirine photophore
Kempin, Uwe,Kanaoka, Yuichi,Hatanaka, Yasumam
, p. 465 - 468 (2007/10/03)
Synthesis of a 3-phenyl-3-trifluoromethyldiazirine derivative having a cleavable 1,2-diol moiety for photocross-linking technique is described. An ester of cinnamic acid derivative was prepared by the Wittig reaction of 2-methoxy-4-[3-trifluoromethyl-3H-diazirin-3-yl]benzaldehyde which can be readily prepared by the Friedel-Crafts reaction of corresponding phenyldiazirine. The osmium oxidation of the olefinic bond gave the desired diol derivative, ethyl 2,3-dihydroxy-3-[2-methoxy-4-(3-trifluoromethyl-3H-diazirin-3-yl)phenyl] propionate, in a high yield. The cleavability of the diol group was confirmed by the conventional periodate oxidation to give the starting aldehyde.
A versatile approach for functionalization of 3-aryl-3-trifluoromethyldiazirine photophor
Hashimoto, Makoto,Kanaoka, Yuichi,Hatanaka, Yasumaru
, p. 119 - 122 (2007/10/03)
We introduce here a novel and simple method for the carbonylation of (alkoxyphenyl)diazirine. 3-(3-Methoxyphenyl)-3-trifluoromethyldiazirine was found to be stable under a typical Friedel-Crafts reaction producing carboxaldehyde derivatives of methoxyphen
