877667-30-6Relevant academic research and scientific papers
CARBENE MASS TAGGING
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Page/Page column 22, (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
Alternative one-pot synthesis of (trifluoromethyl)phenyldiazirines from tosyloxime derivatives: Application for new synthesis of optically pure diazirinylphenylalanines for photoaffinity labeling
Wang, Lei,Murai, Yuta,Yoshida, Takuma,Ishida, Akiko,Masuda, Katsuyoshi,Sakihama, Yasuko,Hashidoko, Yasuyuki,Hatanaka, Yasumaru,Hashimoto, Makoto
supporting information, p. 616 - 619 (2015/03/04)
Alternative one-pot synthesis of 3-(trifluoromethyl)-3-phenyldiazirine derivatives from corresponding tosyloximes is developed. The deprotonation of intermediate diaziridine by NH2- is a new approach for construction of diazirine. Moreover, a novel synthesis of optically pure (trifluoromethyl)diazirinylphenylalanine derivatives was attempted involving these methods.
FLUORINATED PHOSPHONIUM IONIC SALTS LINKED TO CARBENE-PRECURSORS
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Page/Page column 26; 30, (2013/08/15)
Fluorinated phosphonium salts are linked to a diazirine moiety. A carbene precursor was photochemically generated from the diazirine to covalently attach the salt to substrates e.g., cotton and paper. Surface-coated substrates were found to have anti-wett
Diazirine-modified gold nanoparticle: Template for efficient photoinduced interfacial carbene insertion reactions
Ismaili, Hossein,Lee, Soo,Workentin, Mark S.
scheme or table, p. 14958 - 14964 (2011/10/31)
Photolysis of a 3-aryl-3-(trifluoromethyl)diazirine-modified monolayer-protected gold nanoparticles (2-C12MPNs), with a core size of 1.8 ± 0.3 nm, in the presence of model carbene trapping reagents leads to efficient, essentially quantitative, modification of the interface via carbene insertion reactions. The utility of carbene insertion reactions as a general approach for the modification of Au-MPNs to provide a breadth of new structures available was demonstrated using acetic acid, methanol, benzyl alcohol, phenol, benzylamine, methyl acrylate, and styrene (10a-g, respectively) as electrophilic carbene trapping agents to form the corresponding modified 3a-g-C12MPNs. The 1.8 ± 0.3 nm gold nanoparticles bearing a diazirine group (2-C12MPNs) were synthesized using the ligand exchange reaction with the requisite 3-aryl-3-(trifluoromethyl) diazirinealkylthiol. The 2-C12MPNs and the resulting products of the reaction on the MPN (3a-g-C12MPN) were fully characterized by IR, 1H NMR, and 19F NMR spectroscopy and, when applicable, transmission electron microscopy (TEM). Verification for the 3a-g-C 12MPNs was accomplished by comparison of the spectral data to those of obtained for the photoreactions of 3-(3-methoxyphenyl)-3-(trifluoromethyl)- 3H-diazirine as a model with 10a-g.
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.
A Novel Family of Aromatic Diazirines for Photoaffinity Labeling
Hatanaka, Yasumaru,Hashimoto, Makoto,Kurihara, Hiroko,Nakayama, Hitoshi,Kanaoka, Yuichi
, p. 383 - 387 (2007/10/02)
A series of simple methods for modifying diazirines bearing an aromatic ring has been accomplished.This first versatile approach involving direct substitution on the aromatic ring of diazirines has been achieved by means of the aromatic thallation of (alkoxyphenyl)diazirines.Introduction of the thallium moiety was successfully followed by nitration, iodination, or palladium-catalyzed carbonylation to give a family of substituted aryldiazirines useful for photolabeling.For instance, diazirines labeled with a nitro group can be detected by spectrophotometric methods, and those labeled with an iodo group can be useful in tracer experiments.The (methoxyphenyl)diazirines were also found to be stable under certain demethylation conditions, thus providing a potential source of diazirines with modifiable phenol hydroxyl groups.By means of this approach, a spacer arm to link diazirines with ligands was readily introduced.Radioactive diazirines labeled with carbon-14 or tritium were also prepared using this method.All the new diazirines were derived from a pair of simple (methoxyphenyl)diazirines.The ease of derivatization of the (alkoxyphenyl)diazirines described here may offer a practical approach to simplify the time-consuming methods currently used for diazirine synthesis.
