930423
CP-alkyne
≥95%
Synonym(s):
2,4,6-Trimethyl-1-(methyl((pent-4-yn-1-yloxy)carbonyl)amino)pyridin-1-ium tetrafluoroborate
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About This Item
Empirical Formula (Hill Notation):
C15H21BF4N2O2
Molecular Weight:
348.14
UNSPSC Code:
41116164
NACRES:
NA.22
Assay:
≥95%
Form:
liquid
InChI key
JEYOQLIMTNLUGZ-UHFFFAOYSA-N
SMILES string
CC1=CC(C)=[N+](N(C(OCCCC#C)=O)C)C(C)=C1.F[B-](F)(F)F
description
Application: Chemoproteomics
assay
≥95%
form
liquid
storage temp.
−20°C
Quality Level
Application
CP-alkyne is a probe that can be used to photochemically label tryptophans. 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
1. Profiling the proteome-wide selectivity of diverse electrophiles
2. A quantitative thiol reactivity profiling platform to analyze redox and electrophile reactive cysteine proteomes
3. Ethynylation of Cysteine Residues: From Peptides to Proteins in Vitro and in Living Cells
4. A Chemoproteomic Platform To Assess Bioactivation Potential of Drugs
5. Inhibition of Zinc-Dependent Histone Deacetylases with a Chemically Triggered Electrophile
6. Reversibility of Covalent Electrophile-Protein Adducts and Chemical Toxicity
2. A quantitative thiol reactivity profiling platform to analyze redox and electrophile reactive cysteine proteomes
3. Ethynylation of Cysteine Residues: From Peptides to Proteins in Vitro and in Living Cells
4. A Chemoproteomic Platform To Assess Bioactivation Potential of Drugs
5. Inhibition of Zinc-Dependent Histone Deacetylases with a Chemically Triggered Electrophile
6. Reversibility of Covalent Electrophile-Protein Adducts and Chemical Toxicity
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Profiling the proteome-wide selectivity of diverse electrophiles
Patrick R. A. Zanon ,Fengchao Yu, et al
ChemRxiv : the preprint server for chemistry (2021)
Zarko V Boskovic et al.
ACS chemical biology, 11(7), 1844-1851 (2016-04-12)
Unbiased binding assays involving small-molecule microarrays were used to identify compounds that display unique patterns of selectivity among members of the zinc-dependent histone deacetylase family of enzymes. A novel, hydroxyquinoline-containing compound, BRD4354, was shown to preferentially inhibit activity of HDAC5
A H El-Khatib et al.
Journal of mass spectrometry : JMS, 52(8), 543-549 (2017-06-04)
1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) derivatives are applied in quantitative proteomics owing to their ability to react with different functional groups, to harbor lanthanoides and hence their compatibility with molecular and elemental mass spectrometry. The new DOTA derivatives, namely Ln-MeCAT-Click and Ln-DOTA-Dimedone
De Lin et al.
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
Yide He et al.
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
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