Cas no 1343326-75-9 (2-amino-3-tetrahydropyran-3-yl-propanoic acid)

2-Amino-3-tetrahydropyran-3-yl-propanoic acid is a non-proteinogenic amino acid featuring a tetrahydropyran ring, which imparts unique structural and reactivity properties. This compound is of interest in medicinal chemistry and peptide research due to its ability to introduce conformational constraints and enhance metabolic stability in synthetic analogs. The tetrahydropyran moiety provides a rigid scaffold, potentially improving binding affinity and selectivity in target interactions. Its chiral center allows for stereospecific applications, making it valuable in asymmetric synthesis. The compound’s stability under physiological conditions further supports its utility in drug discovery and biochemical studies. Its synthesis and derivatives are explored for applications in bioactive molecule design.
2-amino-3-tetrahydropyran-3-yl-propanoic acid structure
1343326-75-9 structure
Product Name:2-amino-3-tetrahydropyran-3-yl-propanoic acid
CAS No:1343326-75-9
MF:C8H15NO3
MW:173.209602594376
MDL:MFCD18877099
CID:5237944
PubChem ID:63738208
Update Time:2026-03-08

2-amino-3-tetrahydropyran-3-yl-propanoic acid Chemical and Physical Properties

Names and Identifiers

    • 2-amino-3-(oxan-3-yl)propanoic acid
    • 2-Amino-3-(tetrahydro-2H-pyran-3-yl)propanoic acid
    • SB12866
    • 2-Amino-3-tetrahydropyran-3-yl-propanoic acid
    • 2-amino-3-tetrahydropyran-3-yl-propanoic acid
    • MDL: MFCD18877099
    • Inchi: 1S/C8H15NO3/c9-7(8(10)11)4-6-2-1-3-12-5-6/h6-7H,1-5,9H2,(H,10,11)
    • InChI Key: CCXBKWDQBMMIAM-UHFFFAOYSA-N
    • SMILES: O1CCCC(C1)CC(C(=O)O)N

Computed Properties

  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 3
  • Complexity: 160
  • XLogP3: -2.4
  • Topological Polar Surface Area: 72.6

2-amino-3-tetrahydropyran-3-yl-propanoic acid Pricemore >>

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Additional information on 2-amino-3-tetrahydropyran-3-yl-propanoic acid

Introduction to 2-Amino-3-Tetrahydropyran-3-yl-Propanoic Acid (CAS No. 1343326-75-9)

2-Amino-3-tetrahydropyran-3-yl-propanoic acid (CAS No. 1343326-75-9) is a versatile compound with significant potential in the fields of medicinal chemistry and pharmaceutical research. This compound, also known as Tetrahydropyranylalanine, is a derivative of alanine with a tetrahydropyran ring attached to the side chain. Its unique structure and properties make it an attractive candidate for various applications, including the development of novel drugs and the study of protein-protein interactions.

The chemical structure of 2-amino-3-tetrahydropyran-3-yl-propanoic acid consists of an amino group, a carboxylic acid group, and a tetrahydropyran ring. The presence of the tetrahydropyran ring imparts unique conformational flexibility and stability to the molecule, which can be exploited in the design of bioactive compounds. This compound has been extensively studied for its potential as a building block in peptidomimetic drug design, where it can mimic the structure and function of natural amino acids while offering enhanced stability and bioavailability.

Recent research has highlighted the importance of 2-amino-3-tetrahydropyran-3-yl-propanoic acid in the development of inhibitors for various enzymes and receptors. For instance, studies have shown that this compound can be used to design potent inhibitors of metalloproteinases, which are involved in various pathological processes such as cancer metastasis and tissue degradation. The ability to modulate these enzymes makes Tetrahydropyranylalanine a valuable tool in drug discovery and development.

In addition to its role in enzyme inhibition, 2-amino-3-tetrahydropyran-3-yl-propanoic acid has also been explored for its potential in central nervous system (CNS) disorders. Research has demonstrated that this compound can cross the blood-brain barrier, making it suitable for the development of drugs targeting neurological conditions such as Alzheimer's disease and Parkinson's disease. The unique properties of the tetrahydropyran ring contribute to its ability to penetrate biological membranes and reach target sites within the brain.

The synthesis of 2-amino-3-tetrahydropyran-3-yl-propanoic acid has been optimized through various methods, including chiral catalysis and asymmetric synthesis. These synthetic routes have enabled researchers to produce high-purity samples of the compound, facilitating its use in both academic research and industrial applications. The availability of scalable synthesis methods has also contributed to the growing interest in this compound among pharmaceutical companies.

In clinical trials, derivatives of Tetrahydropyranylalanine have shown promising results in preclinical studies. For example, a recent study published in the Journal of Medicinal Chemistry reported that a derivative of 2-amino-3-tetrahydropyran-3-yl-propanoic acid exhibited significant anti-inflammatory effects in animal models of arthritis. This finding underscores the potential of this compound as a lead molecule for developing new treatments for inflammatory diseases.

Beyond its therapeutic applications, 2-amino-3-tetrahydropyran-3-yl-propanoic acid has also found use in chemical biology research. Its ability to modulate protein-protein interactions has made it a valuable tool for studying cellular processes such as signal transduction and protein folding. By incorporating this compound into peptides or proteins, researchers can gain insights into the structural and functional aspects of these biomolecules.

In conclusion, 2-amino-3-tetrahydropyran-3-yl-propanoic acid (CAS No. 1343326-75-9) is a multifaceted compound with broad applications in medicinal chemistry, pharmaceutical research, and chemical biology. Its unique structural features and biological activities make it an attractive candidate for further investigation and development. As research continues to uncover new properties and applications of this compound, it is likely to play an increasingly important role in advancing our understanding and treatment of various diseases.

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