Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

806536

Sigma-Aldrich

APN-Maleimide

Synonym(s):

3-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl)propiolonitrile, MAPN

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C13H6N2O2
Molecular Weight:
222.20
UNSPSC Code:
12352111
PubChem Substance ID:
329769017
NACRES:
NA.22

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

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCQ2805

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Oleksandr Koniev et al.
Bioconjugate chemistry, 26(9), 1863-1867 (2015-09-04)
Thiols are among the most frequently used functional groups in the field of bioconjugation. While there exists a variety of heterobifunctional reagents that allow for coupling thiols to other functions (e.g., amines, carboxylic acids), there is no specific reagent for
Sergii Kolodych et al.
Bioconjugate chemistry, 26(2), 197-200 (2015-01-24)
Amine-to-thiol coupling is the most common route for the preparation of antibody-drug conjugates (ADC). It is usually achieved by using heterobifunctional reagents possessing an activated ester at one end and a maleimide group at the other. However, maleimide-based conjugates were

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service