Cas no 117235-10-6 (3-Mercaptopropionic acid NHS ester)

3-Mercaptopropionic acid NHS ester is a reactive crosslinking agent commonly used in bioconjugation and protein modification. Its key functional groups include an NHS ester, which reacts efficiently with primary amines to form stable amide bonds, and a thiol group, enabling subsequent conjugation with maleimide- or haloacetyl-containing molecules. This bifunctional reagent is particularly useful for introducing sulfhydryl groups into biomolecules or creating heterobifunctional crosslinks. The compound offers high reactivity under mild aqueous conditions, ensuring compatibility with sensitive biological samples. Its compact structure minimizes steric hindrance, facilitating efficient conjugation. Typical applications include antibody-drug conjugate synthesis, peptide modification, and surface functionalization for biosensor development. Proper handling requires anhydrous conditions to preserve NHS ester reactivity.
3-Mercaptopropionic acid NHS ester structure
117235-10-6 structure
Product Name:3-Mercaptopropionic acid NHS ester
CAS No:117235-10-6
MF:C7H9NO4S
MW:203.215660810471
MDL:MFCD28964889
CID:1100466
PubChem ID:58596382
Update Time:2025-05-22

3-Mercaptopropionic acid NHS ester Chemical and Physical Properties

Names and Identifiers

    • 3-mercapto-Propanoic acid 2,5-dioxo-1-pyrrolidinyl ester
    • (2,5-dioxopyrrolidin-1-yl) 3-sulfanylpropanoate
    • 1-(3-mercapto-1-oxopropoxy)-2,5-Pyrrolidinedione
    • 2,5-PYRROLIDINEDIONE, 1-(3-MERCAPTO-1-OXOPROPOXY)-
    • NHS ester
    • 3-Mercaptopropionic acid NHS ester
    • 3-Mercaptopropionic acid NHS ester?
    • 3-Mercaptopropanyl-N-hydroxysuccinimide ester
    • 2,5-Dioxopyrrolidin-1-yl 3-mercaptopropanoate
    • 117235-10-6
    • CS-0120080
    • DTXSID50729451
    • Propanoic acid, 3-mercapto-, 2,5-dioxo-1-pyrrolidinyl ester
    • 2,5-DIOXOPYRROLIDIN-1-YL 3-SULFANYLPROPANOATE
    • HY-136159
    • SY292209
    • MFCD28964889
    • E89079
    • DA-31182
    • 1-[(3-Sulfanylpropanoyl)oxy]pyrrolidine-2,5-dione
    • SCHEMBL2454641
    • AS-80009
    • MDL: MFCD28964889
    • Inchi: 1S/C7H9NO4S/c9-5-1-2-6(10)8(5)12-7(11)3-4-13/h13H,1-4H2
    • InChI Key: UTBOEPMMEANMPS-UHFFFAOYSA-N
    • SMILES: SCCC(=O)ON1C(CCC1=O)=O

Computed Properties

  • Exact Mass: 203.02527
  • Monoisotopic Mass: 203.02522894g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 4
  • Complexity: 237
  • 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: -0.5
  • Topological Polar Surface Area: 64.7?2

Experimental Properties

  • PSA: 63.68

3-Mercaptopropionic acid NHS ester Security Information

  • Hazardous Material transportation number:NONH for all modes of transport
  • Storage Condition:2-8°C

3-Mercaptopropionic acid NHS ester Pricemore >>

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Additional information on 3-Mercaptopropionic acid NHS ester

3-Mercaptopropionic Acid NHS Ester: A Comprehensive Overview

3-Mercaptopropionic acid NHS ester (CAS No. 117235-10-6) is a versatile compound widely utilized in various fields of chemistry and biology. This compound, also known as N-hydroxysuccinimide ester of 3-mercaptopropionic acid, is a key reagent in the synthesis of bioconjugates, drug delivery systems, and diagnostic tools. Its unique structure combines the reactivity of a mercapto group with the biocompatibility of an NHS ester, making it an invaluable tool in modern chemical research and applications.

The NHS ester functional group in 3-mercaptopropionic acid NHS ester is highly reactive towards nucleophilic attack, particularly by amines and thiols. This property enables it to act as a coupling agent in the formation of amide or thioether bonds. Recent studies have highlighted its role in click chemistry, where it facilitates rapid and selective reactions under mild conditions. For instance, researchers have employed this compound to develop novel crosslinking agents for tissue engineering applications, demonstrating its potential in creating robust biomaterials.

One of the most significant advancements involving 3-mercaptopropionic acid NHS ester is its application in drug delivery systems. By conjugating this compound with therapeutic agents, scientists have been able to enhance drug stability, targeting efficiency, and bioavailability. A recent study published in *Nature Communications* demonstrated the use of this compound to create stimuli-responsive nanoparticles that release drugs in response to specific physiological conditions, such as pH changes or enzymatic activity.

In the field of diagnostics, 3-mercaptopropionic acid NHS ester has been instrumental in the development of biosensors and immunoassays. Its ability to form stable covalent bonds with proteins and other biomolecules makes it ideal for immobilizing enzymes or antibodies onto surfaces. For example, researchers have utilized this compound to create highly sensitive sensors for detecting biomarkers associated with diseases such as cancer and diabetes.

The synthesis of 3-mercaptopropionic acid NHS ester involves a two-step process: first, the activation of 3-mercaptopropionic acid using carbonyl diimides such as dicyclohexylcarbodiimide (DCC), followed by coupling with N-hydroxysuccinimide (NHS). This method ensures high purity and stability of the final product. Recent optimizations in this synthesis process have focused on improving yield and reducing reaction time, making it more accessible for large-scale production.

Despite its numerous applications, the use of 3-mercaptopropionic acid NHS ester is not without challenges. The reactivity of its NHS ester group can sometimes lead to unintended side reactions if not properly controlled. To address this issue, researchers have explored the use of protecting groups or alternative activation strategies to enhance selectivity during coupling reactions.

In conclusion, 3-mercaptopropionic acid NHS ester (CAS No. 117235-10-6) is a multifaceted compound with a wide range of applications in chemistry and biology. Its unique properties continue to drive innovative research across various disciplines, from drug delivery to diagnostics. As advancements in synthetic methods and application techniques unfold, this compound is poised to play an even more critical role in future scientific discoveries.

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