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911798

Sigma-Aldrich

N-(4-Bromophenyl)-N-phenylacrylamide

≥95%

Sinónimos:

Electrophilic scout fragment, KB05, Scout fragment for targetable cysteine

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About This Item

Fórmula empírica (notación de Hill):
C15H12BrNO
Número de CAS:
1956368-15-2
Peso molecular:
302.17
MDL number:
MFCD32695613
UNSPSC Code:
12352200
NACRES:
NA.22

Quality Level

100

assay

≥95%

form

(Powder or crystals or solid or chunks)

storage temp.

2-8°C

SMILES string

Brc1ccc(cc1)N(c2ccccc2)C(=O)C=C

InChI

1S/C15H12BrNO/c1-2-15(18)17(13-6-4-3-5-7-13)14-10-8-12(16)9-11-14/h2-11H,1H2

InChI key

WFQQVUPOAKOTGT-UHFFFAOYSA-N

Application

N-(4-Bromophenyl)-N-phenylacrylamide is a cysteine-reactive small-molecule fragment for chemoproteomic and ligandability studies for both traditionally druggable proteins as well as ″undruggable,″ or difficult-to-target, proteins. This fragment electrophile, or ″scout″ fragment, can be used alone in fragment-based covalent ligand discovery or incorporated into bifunctional tools such as electrophilic PROTAC® molecules for targeted protein degradation as demonstrated by the Cravatt Lab for E3 ligase discovery.

Other Notes

Technology Spotlight: Proteomic Ligandability Assessment

Proteome-wide covalent ligand discovery in native biological systems

Electrophilic PROTACs that degrade nuclear proteins by engaging DCAF16

Legal Information

PROTAC is a registered trademark of Arvinas Operations, Inc., and is used under license

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Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

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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
Xiaoyu Zhang et al.
Nature chemical biology, 15(7), 737-746 (2019-06-19)
Ligand-dependent protein degradation has emerged as a compelling strategy to pharmacologically control the protein content of cells. So far, however, only a limited number of E3 ligases have been found to support this process. Here, we use a chemical proteomic

Artículos

Proteomic Ligandability Assessment

Ligandability describes the propensity of a protein target to bind a small molecule with high affinity. It is a precursor to evaluating druggability, which requires more advanced translational pharmacological effects and drug-like properties in vivo.

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