m-Maleimidobenzoyl-N-hydroxysulfosuccinimide ester(Sulfo-MBS) - ≥80% , CAS No.92921-25-0

CAS: 92921-25-0 Cat. No.: M293201 Molecular Weight: 416.3 EC Number: 810-567-3

GRADE & PURITY ≥80%

Synonyms

Sulfo-MBS Crosslinker|103848-62-0|m-Maleimidobenzoyl-N-hydroxysulfosuccinimide ester|92921-25-0|1-[3-(2,5-dioxopyrrol-1-yl)benzoyl]oxy-2,5-dioxopyrrolidine-3-sulfonic acid|3-Maleimidobenzoic acid N-hydroxysulfosuccinimide ester|Sulpho-mbs|Sulfo-MBS Cross

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

MBS and its water-soluble analog Sulfo-MBS are heterobifunctional crosslinkers that contain N-hydroxysuccinimide (NHS) ester and maleimide groups that allow covalent conjugation of amine- and sulfhydryl-containing molecules. NHS esters react with primary amines at pH 7-9 to form amide bonds, while maleimides react with sulfhydryl groups at pH 6.5-7.5 to form stable thioether bonds. In aqueous solutions, hydrolytic degradation of the NHS ester is a competing reaction whose rate increases with pH. The maleimide group is more stable than the NHS-ester group but will slowly hydrolyze and also lose its reaction specificity for sulfhydryls at pH values > 7.5. For these reasons, conjugation experiments involving these crosslinkers are usually performed at pH 7.2-7.5, with the NHS-ester (amine-targeted) reaction being accomplished before or simultaneously with the maleimide (sulfhydryl-targeted) reaction.

Specifications

Synonyms

Sulfo-MBS Crosslinker | 103848-62-0 | m-Maleimidobenzoyl-N-hydroxysulfosuccinimide ester | 92921-25-0 | 1-[3-(2, 5-dioxopyrrol-1-yl)benzoyl]oxy-2, 5-dioxopyrrolidine-3-sulfonic acid | 3-Maleimidobenzoic acid N-hydroxysulfosuccinimide ester | Sulpho-mbs | Sulfo-MBS Cross

Specifications & Purity

≥80%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥80%

Names and Identifiers

• Canonical Smiles: C1C(C(=O)N(C1=O)OC(=O)C2=CC(=CC=C2)N3C(=O)C=CC3=O)S(=O)(=O)O
• IUPAC Name: 1-[3-(2,5-dioxopyrrol-1-yl)benzoyl]oxy-2,5-dioxopyrrolidine-3-sulfonic acid
• InChIKey: DIYPCWKHSODVAP-UHFFFAOYSA-N
• INCHI: 1S/C15H10N2O9S/c18-11-4-5-12(19)16(11)9-3-1-2-8(6-9)15(22)26-17-13(20)7-10(14(17)21)27(23,24)25/h1-6,10H,7H2,(H,23,24,25)
• Isomeric SMILES: C1C(C(=O)N(C1=O)OC(=O)C2=CC(=CC=C2)N3C(=O)C=CC3=O)S(=O)(=O)O
• Molecular Weight: 416.3
• Reaxy-Rn: 14351872
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=14351872&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Acylaminobenzoic acid and derivatives
• Alternative Parents: Phenylpyrrolines Benzoyl derivatives Maleimides Pyrrolidine-2-ones N-substituted carboxylic acid imides Sulfonyls Pyrroles Organosulfonic acids Dicarboximides Alkanesulfonic acids Lactams Carboxylic acid salts Monocarboxylic acids and derivatives Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic salts Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Acylaminobenzoic acid or derivatives - 1-phenylpyrroline - Benzoyl - Maleimide - 2-pyrrolidone - Pyrrolidone - Carboxylic acid imide, n-substituted - Alkanesulfonic acid - Sulfonyl - Organosulfonic acid - Organosulfonic acid or derivatives - Organic sulfonic acid or derivatives - Pyrroline - Pyrrolidine - Pyrrole - Dicarboximide - Carboxylic acid imide - Lactam - Carboxylic acid salt - Azacycle - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic salt - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: Moisture sensitive
• Molecular Weight: 394.300 g/mol
• XLogP3: -0.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 394.011 Da
• Monoisotopic Mass: 394.011 Da
• Topological Polar Surface Area: 164.000 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 839.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1