SM(PEG)12(PEGylated, long-chain SMCC crosslinker) - ≥98%(titration) , CAS No.756525-92-5

CAS: 756525-92-5 Cat. No.: S638993 Peso molecular: 865.92 Número EC: 824-653-3

GRADE & PURITY ≥98%(titration)

Storage

Protected from light,Store at -20°C,Argon charged,Desiccated

Shipped In

Ice chest + Ice pads

Descripción general

Product introduction：

SM(PEG)n is a series of amine-to-sulfhydryl crosslinkers that differ in length from 17.6 to 95.2 angstroms as a result of polyethylene glycol spacer arms containing n equals 2 to 24 ethylene glycol units.

Features of SM(PEG)12:

• Reactive groups:NHS ester andmaleimide
• Reactive toward: amino and sulfhydryl groups
• Irreversibly crosslink proteins or peptides by flexible PEG spacer arms
• Polyethylene glycol spacer arms help maintain conjugate solubility
• Pure compound with defined structure and molecular weight, ensuring reproducible protein-modification effects
• PEG spacer provides unique advantages, including increased stability, reduced tendency toward aggregation and reduced immunogenicity
• Ideal for performing controlled, two-step protein conjugations (seeSulfo-SMCC)

SM(PEG)n NHS- and maleimide-activated PEG compounds for crosslinking between primary amines (NH2) and sulfhydryl (SH) groups in proteins and other molecules. A complete set of compounds are offered, each having the same heterobifunctional structure (NHS-PEGn-Maleimide) but differing in the number of discrete ethylene glycol units ( n = 2, 4, 6, 8, 12 or 24). The N-hydroxysuccinimide ester (NHS) group reacts specifically and efficiently with lysine and N-terminal amino groups at pH 7-9 to form stable amide bonds. The maleimide group reacts with reduced sulfhydryls at pH 6.5-7.5 to form stable thioether bonds.

Alternative Names for SM(PEG)n:
• NHS-dPEG-Mal
• Mal-PEG NHS ester
• NHS-PEO-Maleimide
• Succinimidyl-dPEG-maleimide
• Succinimide-Maleimide PEG

Why use crosslinkers with polyethylene glycol (PEG) spacer arms?
PEG-containing reagents have been used to modify proteins to provide specific advantages. Protein PEGylation can improve the stability of the modified protein, protect it from proteolytic digestion, increase its half life in a biological application, mask it from causing an immunogenic response, decrease its antigenicity or potential toxicity, improve its solubility, diminish the potential for aggregation, and minimize interference for both in vitro and in vivo applications. Polyethylene glycol has these effects because it is nontoxic, nonimmunogenic, hydrophilic, water soluble and highly flexible.

Advantages of discrete-length polyethylene glycol compounds:
These reagents are specially synthesized, resulting in homogeneous compounds of defined molecular weight, characterized by discrete chain lengths, providing a greater ability to optimize and characterize surface protein modifications. Typical preparations of PEG compounds are a heterogeneous mixtures composed of a distribution of chain lengths with a specified average molecular weight or approximate number of PEG subunits.

Specifications

Especificaciones y pureza

≥98%(titration)

Condiciones de almacenamiento de almacenamiento

Protected from light, Store at -20°C, Argon charged, Desiccated

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Pureza

≥98%(titration)

Nombres e identificadores

• Sonrisas canónicas: C1CC(=O)N(C1=O)OC(=O)CCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCNC(=O)CCN2C(=O)C=CC2=O
• IUPAC Name: (2,5-dioxopyrrolidin-1-yl) 3-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
• InChIKey: LWNZLSLPQXOOAO-UHFFFAOYSA-N
• INCHI: 1S/C38H63N3O19/c42-33(5-8-40-34(43)1-2-35(40)44)39-7-10-49-12-14-51-16-18-53-20-22-55-24-26-57-28-30-59-32-31-58-29-27-56-25-23-54-21-19-52-17-15-50-13-11-48-9-6-38(47)60-41-36(45)3-4-37(41)46/h1-2H,3-32H2,(H,39,42)
• Isómeros SMILES: C1CC(=O)N(C1=O)OC(=O)CCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCNC(=O)CCN2C(=O)C=CC2=O
• Peso molecular: 865.92
• Reaxy-Rn: 11457128
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=11457128&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Pyrrolidines
      • Subclass Pyrrolidones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Pyrrolidines
• Subclass: Pyrrolidones
• Intermediate Tree Nodes: Not available
• Direct Parent: Maleimides
• Alternative Parents: Pyrrolidine-2-ones N-substituted carboxylic acid imides Pyrrolines Dicarboximides Tertiary amines Secondary carboxylic acid amides Lactams Amino acids and derivatives Monocarboxylic acids and derivatives Dialkyl ethers Azacyclic compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Maleimide - Carboxylic acid imide, n-substituted - 2-pyrrolidone - Carboxylic acid imide - Dicarboximide - Pyrroline - Tertiary amine - Secondary carboxylic acid amide - Amino acid or derivatives - Carboxamide group - Lactam - Azacycle - Carboxylic acid derivative - Dialkyl ether - Ether - Monocarboxylic acid or derivatives - Amine - Organic oxide - Hydrocarbon derivative - Carbonyl group - Organooxygen compound - Organic oxygen compound - Organic nitrogen compound - Organonitrogen compound - Aliphatic heteromonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as maleimides. These are compounds containing a 2,5-pyrroledione moiety.
• 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

Propiedades químicas y físicas

• Solubilidad: Water
• Sensibilidad: Moisture and light sensitive