Cas no 754176-53-9 ((3S)-3-amino-3-cyclopropyl-propanoic acid)

(3S)-3-Amino-3-cyclopropyl-propanoic acid is a chiral non-proteinogenic amino acid featuring a cyclopropyl group, which confers unique structural and reactivity properties. The stereospecific (S)-configuration at the 3-position enhances its utility in asymmetric synthesis and pharmaceutical applications. The cyclopropyl ring introduces steric constraints and electronic effects, making it valuable for modifying peptide backbones or designing enzyme inhibitors. This compound serves as a versatile intermediate in medicinal chemistry, particularly for developing bioactive molecules with improved metabolic stability. Its high purity and well-defined stereochemistry ensure reproducibility in research and industrial processes. The amino and carboxyl functional groups allow for further derivatization, facilitating its incorporation into complex molecular architectures.
(3S)-3-amino-3-cyclopropyl-propanoic acid structure
754176-53-9 structure
Product Name:(3S)-3-amino-3-cyclopropyl-propanoic acid
CAS No:754176-53-9
MF:C6H11NO2
MW:129.157041788101
CID:981774
PubChem ID:40423876
Update Time:2025-11-02

(3S)-3-amino-3-cyclopropyl-propanoic acid Chemical and Physical Properties

Names and Identifiers

    • (S)-3-AMINO-3-CYCLOPROPYL-PROPIONIC ACID
    • (3S)-3-AMINO-3-CYCLOPROPYLPROPANOIC ACID
    • AB23543
    • (3S)-3-amino-3-cyclopropyl-propanoic acid
    • EN300-1287821
    • AKOS026733682
    • 754176-53-9
    • CS-0055980
    • (3S)-3-AMINO-3-CYCLOPROPYLPROPANOICACID
    • SCHEMBL21193998
    • F53443
    • Inchi: 1S/C6H11NO2/c7-5(3-6(8)9)4-1-2-4/h4-5H,1-3,7H2,(H,8,9)/t5-/m0/s1
    • InChI Key: IHWFMMMLMIDKCB-YFKPBYRVSA-N
    • SMILES: OC(C[C@@H](C1CC1)N)=O

Computed Properties

  • Exact Mass: 129.078978594g/mol
  • Monoisotopic Mass: 129.078978594g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 3
  • Complexity: 120
  • 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
  • Topological Polar Surface Area: 63.3
  • XLogP3: -2.7

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Additional information on (3S)-3-amino-3-cyclopropyl-propanoic acid

Exploring (3S)-3-amino-3-cyclopropyl-propanoic acid (CAS No. 754176-53-9): A Versatile Chiral Building Block in Modern Chemistry

In the realm of synthetic and medicinal chemistry, (3S)-3-amino-3-cyclopropyl-propanoic acid (CAS No. 754176-53-9) has emerged as a pivotal chiral intermediate. This compound, characterized by its cyclopropyl moiety and amino acid backbone, is increasingly sought after for its role in designing bioactive molecules. Its unique stereochemistry and structural rigidity make it a valuable asset in drug discovery, particularly for targeting G-protein-coupled receptors (GPCRs) and enzyme inhibitors. Researchers are leveraging its chiral purity to enhance the efficacy of peptide-based therapeutics, a trending topic in precision medicine.

The growing interest in small-molecule drugs and bioconjugation techniques has further amplified the demand for (3S)-3-amino-3-cyclopropyl-propanoic acid. Its CAS No. 754176-53-9 is frequently queried in databases like SciFinder and Reaxys, reflecting its industrial relevance. A surge in searches for "chiral synthons for drug development" and "cyclopropyl amino acid derivatives" underscores its alignment with current pharmaceutical trends. Notably, its application in PROTACs (Proteolysis-Targeting Chimeras) and ADC (Antibody-Drug Conjugate) platforms highlights its adaptability to cutting-edge cancer therapeutics.

From a synthetic perspective, the stereoselective synthesis of (3S)-3-amino-3-cyclopropyl-propanoic acid often involves asymmetric hydrogenation or enzymatic resolution, methods widely discussed in green chemistry forums. The compound’s low toxicity profile and compatibility with click chemistry reactions resonate with the industry’s shift toward sustainable methodologies. FAQs such as "How to optimize yield of (3S)-3-amino-3-cyclopropyl-propanoic acid?" or "Applications in peptide mimetics" dominate academic discussions, indicating its interdisciplinary appeal.

Beyond pharmaceuticals, CAS No. 754176-53-9 finds utility in material science, particularly in designing bio-based polymers with enhanced thermal stability. Its carboxylate and amine functionalities enable covalent modifications, a feature exploited in smart materials research. As the demand for biodegradable and high-performance polymers grows, this compound’s role is poised to expand, aligning with global sustainability goals.

In summary, (3S)-3-amino-3-cyclopropyl-propanoic acid (CAS No. 754176-53-9) exemplifies the convergence of chiral synthesis, drug discovery, and green technology. Its multifaceted applications and rising prominence in academic literature and patent filings cement its status as a cornerstone of modern organic chemistry.

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