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Key Documents

927600

Sigma-Aldrich

BrBT-alkyne

≥95%

Synonym(s):

2-Bromo-N-(prop-2-yn-1-yl)benzo[d]thiazole-6-carboxamide

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About This Item

Empirical Formula (Hill Notation):
C11H7BrN2OS
CAS Number:
Molecular Weight:
295.16
UNSPSC Code:
12352101
NACRES:
NA.22

Quality Level

Assay

≥95%

form

powder

storage temp.

−20°C

SMILES string

BrC1=NC2=CC=C(C(NCC#C)=O)C=C2S1

Application

BrBT-alkyne is a probe that can be used to lable cysteines through nucleophilic aromatic substitution. 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

11 - Combustible Solids

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.
Zanon P R A, et al.
Angewandte Chemie (International Edition in English), 2829-2836 (2020)
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

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