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923818

Sigma-Aldrich

N-(But-3-yn-1-yl)-2-(((2-oxo-2H-chromen-7-yl)oxy)methyl)acrylamide

Synonym(s):

Coumarin alkyne CoLDR probe

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About This Item

Empirical Formula (Hill Notation):
C17H15NO4
Molecular Weight:
297.31
NACRES:
NA.22

reaction suitability

reagent type: chemical modification reagent
reaction type: click chemistry

Quality Level

100

functional group

(Alkyne)

storage temp.

2-8°C

SMILES string

O=C1OC2=CC(OCC(C(NCCC#C)=O)=C)=CC=C2C=C1

Related Categories

Application

N-(But-3-yn-1-yl)-2-(((2-oxo-2H-chromen-7-yl)oxy)methyl)acrylamide is a proteomic cysteine probe. As described in Reddi et al, the Nir London lab developed a-substituted N-alkynyl-methacrylamides for covalent ligand directed release chemistry (CoLDR). CoLDR represents a new type of acrylamide-based electrophiles for targeted covalent inhibitor discovery and design. Specifically this CoLDR probe is a coumarin derivative with a terminal alkyne for click chemistry.

Other Notes

Chemical Biology Tools

Click Chemistry Reagents

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Rambabu N Reddi et al.
Journal of the American Chemical Society, 143(13), 4979-4992 (2021-03-26)
Targeted covalent inhibitors are an important class of drugs and chemical probes. However, relatively few electrophiles meet the criteria for successful covalent inhibitor design. Here we describe α-substituted methacrylamides as a new class of electrophiles suitable for targeted covalent inhibitors.

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