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
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description
Application: Chemoproteomics
Quality Level
Assay
≥95%
form
liquid
storage temp.
−20°C
SMILES string
CC1=CC(C)=[N+](N(C(OCCCC#C)=O)C)C(C)=C1.F[B-](F)(F)F
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 Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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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)
Bengt H Gless et al.
The Journal of organic chemistry, 83(17), 10525-10534 (2018-08-07)
The one-pot synthesis and modification of cyclic peptides through a self-cleaving on-resin protocol is described. We apply Dawson's MeDbz linker to achieve direct intramolecular peptide cyclization by thioesterification followed by S → N acyl shift. This native chemical ligation approach
Romain Tessier et al.
Angewandte Chemie (International ed. in English), 59(27), 10961-10970 (2020-04-02)
Current approaches to introduce terminal alkynes for bioorthogonal reactions into biomolecules still present limitations in terms of either reactivity, selectivity, or adduct stability. We present a method for the ethynylation of cysteine residues based on the use of ethynylbenziodoxolone (EBX)
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
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
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