55750-61-3

Basic information

• Product Name: N-Succinimidyl maleimidoacetate
• Synonyms: MALEIMIDOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER;N-SUCCINIMIDYL MALEIMIDOACETATE;a-Maleimidoacetic acid-NHS;N-(α-Maleimidoacetoxy)succinimide Ester(AMAS);1-[2-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-2-oxoethyl]-1H-pyrrole-2,5-dione;N-(α-MaleiMidoacetoxy)succiMide;1H-Pyrrole-2,5-dione, 1-[2-[(2,5-dioxo-1-pyrrolidinyl)oxy]-2-oxoethyl]-;MaleiMidoacetic
• CAS NO: 55750-61-3
• Molecular Formula: C₁₀H₈N₂O₆
• Molecular Weight: 252.18
• Product Categories: Nitric Oxide Reagents;Cross Linking Reagents;Maleimide Derivatives;Crosslinking;Heterobifunctional Cross-Linking Reagents;Protein Modification;Cross Linking Reagents,Maleimide Derivatives;MTS & Sulfhydryl Active Reagents
• Mol File: 55750-61-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 174-175°C
• Boiling Point: 430.1 °C at 760 mmHg
• Flash Point: 213.9 °C
• Appearance: /
• Density: 1.63 g/cm³
• Vapor Pressure: 1.33E-07mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly, Heated, Sonicat
• PKA: -2.69±0.20(Predicted)
• CAS DataBase Reference: N-Succinimidyl maleimidoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: N-Succinimidyl maleimidoacetate(55750-61-3)
• EPA Substance Registry System: N-Succinimidyl maleimidoacetate(55750-61-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 55750-61-3(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

Uses

Different sources of media describe the Uses of 55750-61-3 differently. You can refer to the following data:
1. Maleimidoacetic acid N-hydroxysuccinimide ester is a crosslinking reagent that contains NHS ester- and maleimide-reactive groups at the opposite ends of a 4.4 ? spacer arm. This configuration allows for sequential, two-stage conjugation with amine and sulfhydryl functional groups in the preparation of protein-hapten or protein-protein conjugates.
2. A hetero-bifunctional cross-linking reagent for the preparation of protein-protein or protein-hapten conjugates.
3. A hetero-bifunctional cross-linking reagent for the preparation of protein-protein or protein-hapten conjugates

InChI:InChI=1/C10H8N2O6/c13-6-1-2-7(14)11(6)5-10(17)18-12-8(15)3-4-9(12)16/h1-2H,3-5H2

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 25021-08-3 N,N-maleoyl-glycine 
• 54930-24-4 (Z)-4-((carboxymethyl)amino)-4-oxobut-2-enoic acid 
• 329709-87-7 C₆H₇NO₅ 
• 17686-36-1 (2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetyl chloride 

Downstream Products

• 1567360-68-2 N-((7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-1,2,3,4-tetrahydroquinolin-4-yl)methyl)-2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetamide 

Relevant articles and documents

Synthesis N - maleic imide-based arylalkylic and its succinyl eater of method

The invention provides a method for synthesizing N-maleimidoalkyl acid and succinimido ester thereof, which comprises the following steps: (a) carrying out cyclization reaction on a compound disclosed as Formula (II) and phenyl 4-nitrotrifluoroacetate in an organic solvent in the presence of alkali to obtain N-maleimidoalkyl acid disclosed as Formula (III); and (b) reacting the N-maleimidoalkyl acid disclosed as Formula (III) and an acylation reagent in an organic solvent at reflux temperature to obtain an acyl chloride intermediate disclosed as (IV), reacting the acyl chloride intermediate disclosed as (IV) with N-hydroxy succinimide in an organic solvent in the presence of alkali to obtain the N-maleimidoalkyl acid succinimido ester disclosed as Formula (V). The method has the advantages of simple technique, high yield and high product purity, and is suitable for industrial production. The reaction route is disclosed in the specification.

Synthesis of N-Maleoyl-aminoacids and -peptides

N-Maleoyl-aminoacid-N'-hydroxysuccinimidesters 3 or N-maleoyl-aminobenzoic acids 5 are synthsized from N-maleyl-aminoacids 1 on different ways.N-maleoyl-aminobenzoic-4-nirophenyl-, -2-nitro-phenyl- or 2,4-dinitro-phenylesters 6, 7 and 8 will be obtained from 1 or 5. o-Mercaptoaniline, thiourea or cysteine react with 5 to benzothiazines 9, thiazolidines 10 and 1,4-thiazines 11.From 5 the peptides 12 are yielded.The pentapeptide 13 are formed from 12 by addition of glutathione.

Preparation and some properties of maleimido acids and maleoyl derivatives of peptides.

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