Cas no 116823-32-6 (trans-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid)

Technical Introduction: trans-1-Amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid is a conformationally constrained cyclic β-amino acid derivative, characterized by its unique cyclobutane backbone with both amino and hydroxymethyl functional groups in a trans configuration. This structural motif enhances rigidity, making it valuable in peptide design and medicinal chemistry for modulating conformational stability and bioavailability. The hydroxymethyl group offers additional synthetic versatility for further functionalization, while the amino acid core maintains compatibility with standard peptide coupling protocols. Its stereochemistry and functional group arrangement contribute to selective interactions in biological systems, supporting applications in drug discovery and biomaterial development. The compound is typically supplied as a high-purity solid, suitable for research and industrial use.
trans-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid structure
116823-32-6 structure
Product Name:trans-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid
CAS No:116823-32-6
MF:C6H11NO3
MW:145.156441926956
MDL:MFCD01318244
CID:132622
PubChem ID:360046
Update Time:2025-11-02

trans-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • Cyclobutanecarboxylicacid, 1-amino-3-(hydroxymethyl)-, trans-
    • Cyclobutanecarboxylic acid, 1-amino-3-(hydroxymethyl)-, trans- (9CI)
    • 1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid
    • trans-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid
    • 1-Amino-3-(hydroxymethyl)cyclobutanecarboxylic acid
    • Cis-1-amino-3-hydroxymethyl-cyclobutane-1-carboxylic acid
    • cis-1-Amino-3-(hydroxymethyl)cyclobutanecarboxylic acid
    • trans-1-Amino-3-(hydroxymethyl)cyclobutanecarboxylic acid
    • NSC621813
    • SB22506
    • AS-
    • NSC-621813
    • CS-0047834
    • SCHEMBL21946032
    • CS-0052645
    • SCHEMBL25662370
    • AKOS023600433
    • MFCD24498278
    • AS-52957
    • Cyclobutanecarboxylic acid,1-amino-3-(hydroxymethyl)-,cis-(9ci)
    • MFCD01318244
    • SY099377
    • 109794-96-9
    • AKOS006339356
    • 116823-32-6
    • (1r,3r)-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid
    • PB48867
    • SCHEMBL12909454
    • EN300-1609239
    • AS-54253
    • cis-1-Amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid
    • Cyclobutanecarboxylic acid, 1-amino-3-(hydroxymethyl)-
    • CS-0056252
    • 1555492-59-5
    • P15911
    • EN300-7168071
    • P17677
    • (1s,3s)-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid
    • SCHEMBL25660685
    • AKOS006339355
    • cis-1-Amino-3-(hydroxymethyl)cyclobutanecarboxylicacid
    • MDL: MFCD01318244
    • Inchi: 1S/C6H11NO3/c7-6(5(9)10)1-4(2-6)3-8/h4,8H,1-3,7H2,(H,9,10)
    • InChI Key: URCBHRLIPUAWTF-UHFFFAOYSA-N
    • SMILES: OCC1CC(C(=O)O)(C1)N

Computed Properties

  • Exact Mass: 145.074
  • Monoisotopic Mass: 145.074
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 2
  • Complexity: 151
  • 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: -3.5
  • Topological Polar Surface Area: 83.6

Experimental Properties

  • Color/Form: Colorless liquid

trans-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid Security Information

  • Storage Condition:20°C

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Additional information on trans-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid

Comprehensive Overview of trans-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid (CAS No. 116823-32-6)

trans-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid, with the CAS number 116823-32-6, is a specialized cyclic amino acid derivative that has garnered significant attention in pharmaceutical and biochemical research. This compound, often abbreviated as trans-ACBC, features a unique cyclobutane backbone with both amino and hydroxymethyl functional groups, making it a versatile building block for drug discovery and peptide engineering. Its structural rigidity and chiral centers contribute to its potential applications in targeting G-protein-coupled receptors (GPCRs) and modulating neurotransmitter systems.

In recent years, the demand for custom amino acids like trans-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid has surged due to their role in developing peptide therapeutics and small-molecule drugs. Researchers are particularly interested in its potential to enhance drug bioavailability and metabolic stability, addressing common challenges in oral drug delivery. The compound’s cyclobutane ring offers conformational constraints that can improve binding affinity to biological targets, a feature highly sought after in cancer immunotherapy and central nervous system (CNS) disorders.

The synthesis of CAS 116823-32-6 typically involves stereoselective methods to ensure the correct trans-configuration, which is critical for its biological activity. Advanced techniques such as asymmetric catalysis and enzymatic resolution are often employed to achieve high enantiomeric purity. This aligns with the growing trend in green chemistry, where sustainable and efficient synthetic routes are prioritized to reduce environmental impact.

From a commercial perspective, trans-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid is available through specialized chemical suppliers and contract research organizations (CROs). Its pricing and availability are influenced by factors such as scale of production, purity grade (e.g., >98% HPLC), and custom modifications. Companies focusing on peptide-based drug development often seek this compound for its ability to introduce structural diversity into lead optimization campaigns.

Emerging studies highlight the potential of trans-ACBC in addressing neurodegenerative diseases, such as Alzheimer’s and Parkinson’s, due to its ability to cross the blood-brain barrier (BBB). This has sparked interest in its use for designing neuroprotective agents and diagnostic probes. Additionally, its application in bioconjugation and prodrug strategies further expands its utility in modern precision medicine.

For researchers exploring structure-activity relationships (SAR), trans-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid serves as a valuable scaffold to investigate molecular interactions and conformational dynamics. Computational tools like molecular docking and quantum mechanics calculations are frequently employed to predict its behavior in complex biological systems. These approaches align with the industry’s shift toward AI-driven drug discovery, where machine learning models accelerate the identification of novel bioactive compounds.

In summary, CAS 116823-32-6 represents a cutting-edge tool in medicinal chemistry and biotechnology, bridging gaps between chemical synthesis and therapeutic innovation. Its multifaceted applications—from drug design to neuroscience research—underscore its importance in advancing personalized healthcare solutions. As the scientific community continues to uncover its potential, this compound is poised to play a pivotal role in shaping the future of bioactive small molecules.

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