930458
OxMet2-alkyne
Synonym(s):
(3-Phenyl-1,2-oxaziridin-2-yl)(4-(prop-2-yn-1-yloxy)piperidin-1-yl)methanone
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description
Application: Chemoproteomics
Quality Level
form
liquid
storage temp.
−20°C
SMILES string
O=C(N1OC1C2=CC=CC=C2)N(CC3)CCC3OCC#C
Application
OxMet2-alkyne is an oxaziridine probe that can be used to label methionines. A method was developed using cysteine-reactive compounds including this one to allow for unbiased analysis of proteomic data in quantitative applications (Zanon et al. 2021). The method uses light or heavy labelling with the isotopically labelled desthiobiotin azide (isoDTB) tag for mass spectrometry analysis (Zanon et al. 2020). Analysis then uses the isotopic tandem orthogonal proteolysis activity-based protein profiling (isoTOP-ABPP) workflow (Weerapana et al. 2010, Backus et al. 2016)
Other Notes
Profiling the proteome-wide selectivity of diverse electrophiles
A quantitative thiol reactivity profiling platform to analyze redox and electrophile reactive cysteine proteomes
Ethynylation of Cysteine Residues: From Peptides to Proteins in Vitro and in Living Cells
A Chemoproteomic Platform To Assess Bioactivation Potential of Drugs
Inhibition of Zinc-Dependent Histone Deacetylases with a Chemically Triggered Electrophile
Reversibility of Covalent Electrophile-Protein Adducts and Chemical Toxicity
A quantitative thiol reactivity profiling platform to analyze redox and electrophile reactive cysteine proteomes
Ethynylation of Cysteine Residues: From Peptides to Proteins in Vitro and in Living Cells
A Chemoproteomic Platform To Assess Bioactivation Potential of Drugs
Inhibition of Zinc-Dependent Histone Deacetylases with a Chemically Triggered Electrophile
Reversibility of Covalent Electrophile-Protein Adducts and Chemical Toxicity
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Description
Pricing
Storage Class
10 - Combustible liquids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Profiling the proteome-wide selectivity of diverse electrophiles
ChemRxiv : the preprint server for chemistry (2021)
Nucleosides, nucleotides & nucleic acids, 40(7), 754-766 (2021-06-29)
We report herein comprehensive investigations of alkylation/sulfur exchange reactions of sulfur-containing substrates including nucleosides such as s2U, m5s2U, s4U, s2A and s2T-incorporated DNA enable by comprehensive screenings of the reagents (2a-2h). It has been proven that iodoacetamide (2a) displays the
Talanta, 134, 468-475 (2015-01-27)
In this work, we present a two-step labeling approach for the efficient tagging with lanthanide-containing complexes. For this purpose, derivatization of the cysteine residues with an alkyne group acting as linker was done before the DOTA complex was introduced using
Chemical research in toxicology, 30(10), 1797-1803 (2017-09-30)
Reactive metabolites (RM) formed from bioactivation of drugs can covalently modify liver proteins and cause mechanism-based inactivation of major cytochrome P450 (CYP450) enzymes. Risk of bioactivation of a test compound is routinely examined as part of lead optimization efforts in
Chemical research in toxicology, 21(12), 2361-2369 (2009-06-24)
The biotin-tagged electrophiles 1-biotinamido-4-(4'-[maleimidoethylcyclohexane]-carboxamido)butane (BMCC) and N-iodoacetyl-N-biotinylhexylenediamine (IAB) have been used as model electrophile probes in complex proteomes to identify protein targets associated with chemical toxicity. Whereas IAB activates stress signaling and apoptosis in HEK293 cells, BMCC does not. Cysteine
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