806536

APN-Maleimide

• Synonym(s): 3-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl)propiolonitrile, MAPN
• Empirical Formula (Hill Notation): C₁₃H₆N₂O₂
• Molecular Weight: 222.20
• UNSPSC Code: 12352111
• PubChem Substance ID: 329769017
• NACRES: NA.22

Properties

• form: powder
• Quality Level: 100
• storage temp.: 2-8°C
• SMILES string: N#CC#CC1=CC=C(N2C(C=CC2=O)=O)C=C1
• InChI: 1S/C13H6N2O2/c14-9-1-2-10-3-5-11(6-4-10)15-12(16)7-8-13(15)17/h3-8H
• InChI key: CHKKXKRQICWZFF-UHFFFAOYSA-N

Description

Application

APN-Maleimide is a bifunctional crosslinker for thiol-to-thiol coupling. The coupling can be performed with high selectivity in biological medium using mild reaction conditions. Due to kinetic resolution the first thiol reacts exclusively with the maleimide residue producing the protein-APN conjugate. This conjugate can be readily coupled with thiol-containing molecules.

Preparation Note

Standard protein labeling procedure (cysteine labeling).

• Dissolve the protein in the appropriate buffer* with pH 6.5-9.0 (e.g. PBS) at 1-10 mg/mL concentration.
• Apply the appropriate amount of the stock solution of the reagent (1-5 molar eq. per free cysteine residue).
• Incubate at room temperature for 10 minutes.
• If necessary, purify the protein-APN conjugate using size exclusion chromatography or ultrafiltration.
• The conjugate can be readily coupled with thiol-containing substrates by incubating the components in aqueous buffer (pH 6.5-9.0) at ambient temperature for 2 hours.

*Note: avoid thiol-containing buffers.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302,H315,H319,H335
• Precautionary Statements: P261 - P264 - P270 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable