Cas no 77856-50-9 ((3R)-3-amino-5-methoxy-5-oxopentanoic acid)

(3R)-3-Amino-5-methoxy-5-oxopentanoic acid is a chiral amino acid derivative characterized by its esterified carboxyl group and free carboxylic acid functionality. This compound serves as a valuable intermediate in organic synthesis and pharmaceutical research, particularly in the development of peptidomimetics and bioactive molecules. The (R)-configuration at the 3-position ensures stereochemical precision, making it suitable for asymmetric synthesis applications. Its methoxy ester group enhances solubility in organic solvents, facilitating further chemical modifications. The presence of both amino and carboxyl groups allows for versatile coupling reactions, enabling integration into complex molecular architectures. This compound is particularly useful in medicinal chemistry for designing enzyme inhibitors or prodrugs due to its structural flexibility and functional group compatibility.
(3R)-3-amino-5-methoxy-5-oxopentanoic acid structure
77856-50-9 structure
Product Name:(3R)-3-amino-5-methoxy-5-oxopentanoic acid
CAS No:77856-50-9
MF:C6H11NO4
MW:161.155842065811
MDL:MFCD22505552
CID:4185093
PubChem ID:11672709
Update Time:2025-06-14

(3R)-3-amino-5-methoxy-5-oxopentanoic acid Chemical and Physical Properties

Names and Identifiers

    • Pentanedioic acid, 3-amino-, monomethyl ester, (R)-
    • Pentanedioic acid, 3-amino-, 1-methyl ester, (3R)-
    • (3R)-3-amino-5-methoxy-5-oxopentanoic acid
    • 77856-50-9
    • SCHEMBL11122916
    • EN300-24794405
    • MDL: MFCD22505552
    • Inchi: 1S/C6H11NO4/c1-11-6(10)3-4(7)2-5(8)9/h4H,2-3,7H2,1H3,(H,8,9)/t4-/m1/s1
    • InChI Key: CTLHFZBIZFOLIK-SCSAIBSYSA-N
    • SMILES: C(OC)(=O)C[C@H](N)CC(O)=O

Computed Properties

  • Exact Mass: 161.06880783Da
  • Monoisotopic Mass: 161.06880783Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 5
  • Complexity: 157
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -3.6
  • Topological Polar Surface Area: 89.6?2

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Additional information on (3R)-3-amino-5-methoxy-5-oxopentanoic acid

Recent Advances in the Study of (3R)-3-amino-5-methoxy-5-oxopentanoic acid (CAS: 77856-50-9)

In recent years, (3R)-3-amino-5-methoxy-5-oxopentanoic acid (CAS: 77856-50-9) has garnered significant attention in the field of chemical biology and pharmaceutical research. This compound, a chiral amino acid derivative, has shown promising potential in various therapeutic applications, including enzyme inhibition, metabolic pathway modulation, and drug delivery systems. The latest studies have focused on its synthesis, biological activity, and potential clinical applications, making it a subject of intense scientific inquiry.

One of the key areas of research involves the optimization of synthetic routes for (3R)-3-amino-5-methoxy-5-oxopentanoic acid. Recent publications highlight novel enzymatic and chemical methods that improve yield and enantiomeric purity, which are critical for its pharmaceutical applications. For instance, a 2023 study demonstrated the use of immobilized lipases in asymmetric synthesis, achieving over 95% enantiomeric excess (ee) under mild conditions. This advancement addresses previous challenges in scalability and cost-effectiveness, paving the way for industrial production.

The biological activity of (3R)-3-amino-5-methoxy-5-oxopentanoic acid has also been a focal point. Researchers have identified its role as a precursor in the biosynthesis of gamma-aminobutyric acid (GABA) analogs, which are relevant in neurological disorders. In vitro and in vivo studies have shown that this compound exhibits moderate inhibitory effects on glutamate decarboxylase, suggesting potential applications in epilepsy and anxiety disorders. Furthermore, its metabolic stability and low toxicity profile make it a viable candidate for further preclinical development.

Another exciting development is the exploration of (3R)-3-amino-5-methoxy-5-oxopentanoic acid in drug delivery systems. Due to its unique physicochemical properties, such as high water solubility and biocompatibility, it has been incorporated into prodrug designs. A recent patent application describes its conjugation with anticancer agents, enhancing their bioavailability and reducing systemic toxicity. This innovation could revolutionize targeted therapy, particularly in oncology.

In conclusion, the latest research on (3R)-3-amino-5-methoxy-5-oxopentanoic acid (CAS: 77856-50-9) underscores its multifaceted potential in chemical biology and pharmaceuticals. From improved synthetic methodologies to novel therapeutic applications, this compound continues to inspire innovation. Future studies are expected to delve deeper into its mechanistic pathways and clinical translation, solidifying its position as a valuable asset in drug discovery and development.

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