38862-24-7
Chemical Structure
2,5-Dioxopyrrolidin-1-yl acrylate
Synonym(s): N-Succinimidyl acrylate
- CAS No.: 38862-24-7
- Formula:C7H7NO4
- Molecular Weight:169.13
IUPAC Name: 2,5-dioxopyrrolidin-1-yl acrylate
InChIKey: YXMISKNUHHOXFT-UHFFFAOYSA-N
SMILES: O=C(C=C)ON1C(CCC1=O)=O
Biological Activity: 2,5-Dioxopyrrolidin-1-yl acrylate (N-Succinimidyl acrylate) is a lysine residue modifier and coupling monomer. 2,5-Dioxopyrrolidin-1-yl acrylate covalently modifies the primary amines of lysine residues on monoclonal anti-horseradish peroxidase IgG antibodies, neutralizes positive charges and replaces them with low-affinity acrylate groups. 2,5-Dioxopyrrolidin-1-yl acrylate inhibits the formation of rapid hard coronas on citrate-coated gold nanoparticles, induces antibody unfolding and loss of antigen-binding function, but does not affect the antigen-binding function of antibodies in free solution. 2,5-Dioxopyrrolidin-1-yl acrylate reacts with the ε-amino groups on lysine residues of L-asparaginase, introduces vinyl groups and generates N-hydroxysuccinimide. 2,5-Dioxopyrrolidin-1-yl acrylate regulates the activity of L-asparaginase[1][2].
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2,5-Dioxopyrrolidin-1-yl acrylate | 99.81% | 2,5-Dioxopyrrolidin-1-yl acrylate (N-Succinimidyl acrylate) is a lysine residue modifier and coupling monomer. 2,5-Dioxopyrrolidin-1-yl acrylate covalently modifies the primary amines of lysine residues on monoclonal anti-horseradish peroxidase IgG antibodies, neutralizes positive charges and replaces them with low-affinity acrylate groups. 2,5-Dioxopyrrolidin-1-yl acrylate inhibits the formation of rapid hard coronas on citrate-coated gold nanoparticles, induces antibody unfolding and loss of antigen-binding function, but does not affect the antigen-binding function of antibodies in free solution. 2,5-Dioxopyrrolidin-1-yl acrylate reacts with the ε-amino groups on lysine residues of L-asparaginase, introduces vinyl groups and generates N-hydroxysuccinimide. 2,5-Dioxopyrrolidin-1-yl acrylate regulates the activity of L-asparaginase. | ||||||||||||||||||||
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References
- [1]. Okyem S, et al. High-Affinity Points of Interaction on Antibody Allow Synthesis of Stable and Highly Functional Antibody-Gold Nanoparticle Conjugates. Bioconjugate chemistry. 2021 Aug 18;32(8):1753-1762. [Content Brief]
- [2]. Shoemaker SG, et al. Synthesis and properties of vinyl monomer/enzyme conjugates. Conjugation of L-asparaginase with N-succinimidyl acrylate. Appl Biochem Biotechnol. 1987 Jun;15(1):11-24. [Content Brief]
