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929271

Sigma-Aldrich

EBX1-alkyne

≥95.0%

Synonym(s):

1-[4-(2-Propyn-1-yloxy)-1-butyn-1-yl]-1,2-benziodoxol-3(1H)-one

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About This Item

Empirical Formula (Hill Notation):
C14H11IO3
CAS Number:
Molecular Weight:
354.14
UNSPSC Code:
12352101
NACRES:
NA.22

Quality Level

Assay

≥95.0%

form

powder

storage temp.

−20°C

SMILES string

O=C(OI1C#CCCOCC#C)C2=C1C=CC=C2

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Application

EBX1-alkyne is a hypervalent iodine reagent used for labeling cysteines. A method was developed using cysteine-reactive compounds including this one to allow for unbiased analysis of proteomic data in quantitative applications. The method uses light or heavy labeling with the isotopically labelled desthiobiotin azide (isoDTB) tag for mass spectrometry analysis. Analysis then uses the isotopic tandem orthogonal proteolysis activity-based protein profiling (isoTOP-ABPP) workflow.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Profiling the proteome-wide selectivity of diverse electrophiles
Zanon, et al.
ChemRxiv : the preprint server for chemistry (2021)
Isotopically Labeled Desthiobiotin Azide (isoDTB) Tags Enable Global Profiling of the Bacterial Cysteinome
Zanon, et al.
Angewandte Chemie (International Edition in English), 2829-2836 (2020)
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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