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927546

Sigma-Aldrich

CA-nitrile

≥95%

Synonym(s):

2-Chloro-N-(4-cyanobutyl)acetamide

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About This Item

Empirical Formula (Hill Notation):
C7H11ClN2O
CAS Number:
1339429-76-3
Molecular Weight:
174.63
MDL number:
MFCD20325219
UNSPSC Code:
12352101
NACRES:
NA.21

Quality Level

100

Assay

≥95%

form

viscous liquid

storage temp.

−20°C

SMILES string

O=C(NCCCCC#N)CCl

Application

CA-nitrile is a negative control probe that can be used for labeling cysteines through alkylation but lacks an alkyne necessary for labeling. A method was developed using cysteine-reactive compounds including this one to allow for unbiased analysis of proteomic data in quantitave applications (Zanon et al. 2021). The method uses light or heavy labeling 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).

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Isotopically Labeled Desthiobiotin Azide (isoDTB) Tags Enable Global Profiling of the Bacterial Cysteinome.
Angewandte Chemie (International Edition in English), 2829-2836 (2020)
Profiling the proteome-wide selectivity of diverse electrophiles.
Zanon P RA, et al.
ChemRxiv : the preprint server for chemistry (2021)
Patrick R A Zanon et al.
Angewandte Chemie (International ed. in English), 59(7), 2829-2836 (2019-11-30)
Rapid development of bacterial resistance has led to an urgent need to find new druggable targets for antibiotics. In this context, residue-specific chemoproteomic approaches enable proteome-wide identification of binding sites for covalent inhibitors. Described here are easily synthesized isotopically labeled
Eranthie Weerapana et al.
Nature, 468(7325), 790-795 (2010-11-19)
Cysteine is the most intrinsically nucleophilic amino acid in proteins, where its reactivity is tuned to perform diverse biochemical functions. The absence of a consensus sequence that defines functional cysteines in proteins has hindered their discovery and characterization. Here we
Keriann M Backus et al.
Nature, 534(7608), 570-574 (2016-06-17)
Small molecules are powerful tools for investigating protein function and can serve as leads for new therapeutics. Most human proteins, however, lack small-molecule ligands, and entire protein classes are considered 'undruggable'. Fragment-based ligand discovery can identify small-molecule probes for proteins

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