Cas no 76078-81-4 (N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE)

N-Succinimidyloxycarbonylpentyl methanethiosulfonate is a heterobifunctional crosslinking reagent designed for precise protein conjugation. The compound features an NHS ester group, enabling efficient amine coupling, and a methanethiosulfonate moiety for selective sulfhydryl modification. This reagent facilitates stable thioether bond formation with cysteine residues while minimizing disulfide exchange, ensuring controlled and site-specific bioconjugation. Its extended pentyl spacer enhances flexibility, reducing steric hindrance in conjugated complexes. Suitable for applications in antibody-drug conjugates, protein labeling, and immobilization, this reagent offers high selectivity and reproducibility under mild reaction conditions. Its water-soluble derivatives further broaden its utility in aqueous environments.
N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE structure
76078-81-4 structure
Product Name:N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE
CAS No:76078-81-4
MF:C11H17NO6S2
MW:323.385781049728
CID:826735
PubChem ID:3614736
Update Time:2025-10-22

N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE Chemical and Physical Properties

Names and Identifiers

    • N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE
    • LogP
    • (2,5-dioxopyrrolidin-1-yl) 6-methylsulfonylsulfanylhexanoate
    • N-Succinimidyloxycar
    • MTS-6-NHS
    • SCHEMBL4862511
    • 76078-81-4
    • 6-[(Methanethisulfonyl)thio]hexanoic acid, N-succinimidyl ester
    • FT-0674720
    • DTXSID20394317
    • AKOS030240286
    • Inchi: 1S/C11H17NO6S2/c1-20(16,17)19-8-4-2-3-5-11(15)18-12-9(13)6-7-10(12)14/h2-8H2,1H3
    • InChI Key: IVIKTTIJCNVVSA-UHFFFAOYSA-N
    • SMILES: S(CCCCCC(=O)ON1C(CCC1=O)=O)S(C)(=O)=O

Computed Properties

  • Exact Mass: 323.04972961g/mol
  • Monoisotopic Mass: 323.04972961g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 7
  • Heavy Atom Count: 20
  • Rotatable Bond Count: 9
  • Complexity: 466
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 0
  • Topological Polar Surface Area: 132?2

Experimental Properties

  • Density: 1.4±0.1 g/cm3
  • Melting Point: 64-67°C
  • Boiling Point: 513.3±52.0 °C at 760 mmHg
  • Flash Point: 264.2±30.7 °C
  • Solubility: Chloroform, DMSOChloroform
  • Stability/Shelf Life: Moisture Sensitive: Desiccate
  • Vapor Pressure: 0.0±1.3 mmHg at 25°C

N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE Security Information

N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE Pricemore >>

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N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE Related Literature

Additional information on N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE

Professional Introduction to Compound with CAS No. 76078-81-4 and Product Name: N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE

The compound in question, identified by the CAS number 76078-81-4, is a specialized chemical reagent that has garnered significant attention in the field of pharmaceutical and biochemical research. This compound, formally known as N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE, plays a pivotal role in the synthesis and modification of peptides and other biomolecules. Its unique chemical structure, featuring a succinimidyloxy carbonyl group and a pentyl methanethiosulfonate moiety, makes it an invaluable tool for researchers aiming to develop novel therapeutic agents.

In recent years, the demand for efficient and reliable methods for peptide coupling has surged due to the increasing complexity of biologics in drug development. The N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE reagent has emerged as a preferred choice for peptide chemists due to its high reactivity and compatibility with a wide range of substrates. This reagent is particularly useful in the formation of amide bonds, which are fundamental to the structure of proteins and peptides. The succinimidyloxy carbonyl group acts as an active ester, facilitating the reaction with nucleophilic amino groups, while the pentyl methanethiosulfonate moiety enhances solubility and stability under various reaction conditions.

Recent advancements in synthetic chemistry have highlighted the importance of this compound in the development of protease inhibitors. Proteases are enzymes that play crucial roles in numerous biological processes, including inflammation and cancer progression. By modifying the active sites of these enzymes, researchers can develop potent inhibitors that target specific diseases. The N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE reagent has been successfully employed in the synthesis of protease inhibitors, demonstrating its efficacy in creating high-affinity binding molecules. For instance, studies have shown its utility in generating inhibitors targeting matrix metalloproteinases (MMPs), which are implicated in tissue degradation and cancer metastasis.

The versatility of this compound is further underscored by its application in solid-phase peptide synthesis (SPPS). SPPS is a widely used technique for constructing complex peptides on resin supports, enabling the efficient production of large-scale libraries for drug discovery. The N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE reagent integrates seamlessly into SPPS protocols, providing researchers with a reliable method for coupling amino acids without compromising yield or purity. This has been particularly beneficial in the synthesis of peptide-based vaccines and diagnostics, where high fidelity is essential.

In addition to its role in peptide synthesis, this compound has found applications in the modification of nucleosides and other heterocyclic compounds. The methanethiosulfonate group introduces a sulfur atom into the molecule, which can be further functionalized to create diverse chemical entities. This property has been exploited in the development of antiviral agents, where sulfur-containing compounds often exhibit enhanced bioactivity. Recent research has demonstrated the use of N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE in synthesizing modified nucleosides that inhibit viral replication by disrupting essential enzymatic pathways.

The chemical stability and reactivity profile of N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE make it an attractive candidate for industrial-scale applications. Its compatibility with standard laboratory equipment and its ability to function under mild conditions reduce the need for harsh reagents or extreme temperatures, thereby lowering costs and improving safety. These attributes align well with current trends toward green chemistry, where minimizing waste and energy consumption are paramount.

From a regulatory perspective, the compound’s well-documented properties have facilitated its approval for use in research settings worldwide. However, as with any chemical reagent, proper handling and storage are essential to ensure optimal performance and safety. Researchers are advised to follow established protocols when working with this compound to prevent degradation or unintended side reactions.

Looking ahead, ongoing research aims to expand the applications of N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE beyond peptide chemistry. Preliminary studies suggest its potential use in modifying lipids and carbohydrates, opening new avenues for drug development. The integration of this reagent into combinatorial chemistry platforms could also lead to novel libraries of bioactive molecules with tailored properties.

In conclusion, N-SUCCINIMIDYLOXYCARBONYLPENTYL METHANETHIOSULFONATE, identified by CAS number 76078-81-4, is a multifaceted chemical reagent that has proven indispensable in modern synthetic biology and pharmaceutical research. Its unique structure enables diverse applications, from peptide coupling to nucleoside modification, while its stability and compatibility make it suitable for both academic and industrial settings. As research continues to uncover new possibilities for this compound, its significance is expected to grow further, contributing to advancements across multiple disciplines.

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