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930423

Sigma-Aldrich

CP-alkyne

≥95%

Synonyme(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

Formule empirique (notation de Hill):
C15H21BF4N2O2
Poids moléculaire :
348.14
Code UNSPSC :
41116164
Nomenclature NACRES :
NA.22

Description

Application: Chemoproteomics

Niveau de qualité

100

Pureté

≥95%

Forme

liquid

Température de stockage

−20°C

Chaîne SMILES 

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)

Autres remarques

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

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°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)
Ping Yu et al.
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
Rui Sun et al.
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
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
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
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