Cas no 13184-41-3 ((3S)-3,7-diaminoheptanoic acid)

(3S)-3,7-Diaminoheptanoic acid is a chiral, non-proteinogenic amino acid featuring two amine functional groups at the C-3 and C-7 positions. Its stereospecific (S)-configuration ensures precise selectivity in synthetic and biochemical applications. The compound serves as a valuable intermediate in peptide synthesis, particularly for introducing branched or modified structures due to its dual reactive sites. Its linear heptanoic acid backbone enhances solubility in aqueous and polar organic solvents, facilitating handling in solution-phase reactions. The presence of both primary amines allows for selective derivatization, making it useful in crosslinking, bioconjugation, and the development of peptidomimetics. This molecule is of interest in medicinal chemistry for its potential role in designing enzyme inhibitors or bioactive ligands.
(3S)-3,7-diaminoheptanoic acid structure
13184-41-3 structure
Product Name:(3S)-3,7-diaminoheptanoic acid
CAS No:13184-41-3
MF:C7H16N2O2
MW:160.214141845703
CID:1229264
PubChem ID:2761529
Update Time:2025-06-08

(3S)-3,7-diaminoheptanoic acid Chemical and Physical Properties

Names and Identifiers

    • Heptanoic acid, 3,7-diamino-, (3S)-
    • (3S)-3,7-diaminoheptanoic acid
    • AmbotzHAA8530
    • 13184-41-3
    • starbld0000058
    • Q27120415
    • (S)-3,7-Diaminoheptanoic acid
    • B3K
    • L-beta-homolysine
    • SCHEMBL289144
    • DTXSID50375816
    • AKOS030213064
    • FD10302
    • CHEBI:41030
    • EN300-1085772
    • Inchi: 1S/C7H16N2O2/c8-4-2-1-3-6(9)5-7(10)11/h6H,1-5,8-9H2,(H,10,11)/t6-/m0/s1
    • InChI Key: PJDINCOFOROBQW-LURJTMIESA-N
    • SMILES: OC(C[C@H](CCCCN)N)=O

Computed Properties

  • Exact Mass: 160.12100
  • Monoisotopic Mass: 160.121177757g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 6
  • Complexity: 117
  • 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: -3.3
  • Topological Polar Surface Area: 89.3?2

Experimental Properties

  • PSA: 89.34000
  • LogP: 1.31800

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Additional information on (3S)-3,7-diaminoheptanoic acid

Research Brief on (3S)-3,7-diaminoheptanoic acid (CAS: 13184-41-3): Recent Advances and Applications

(3S)-3,7-diaminoheptanoic acid (CAS: 13184-41-3) is a non-proteinogenic amino acid that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its unique structural properties and potential therapeutic applications. Recent studies have explored its role as a building block for novel peptide-based therapeutics, enzyme inhibitors, and drug delivery systems. This research brief aims to summarize the latest findings related to this compound, focusing on its synthesis, biological activity, and emerging applications in drug development.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the efficient synthesis of (3S)-3,7-diaminoheptanoic acid via asymmetric catalytic hydrogenation, achieving high enantiomeric purity (>99% ee). The researchers highlighted its utility as a key intermediate in the synthesis of γ-amino acid derivatives, which show promise as modulators of neurotransmitter receptors. The study also reported improved synthetic yields compared to previous methods, making this compound more accessible for pharmaceutical research.

In the area of antimicrobial research, (3S)-3,7-diaminoheptanoic acid has been incorporated into novel antimicrobial peptides (AMPs) that exhibit potent activity against multidrug-resistant bacterial strains. A recent Nature Communications paper described the design of amphipathic peptides containing this amino acid that disrupt bacterial membranes while showing minimal cytotoxicity to mammalian cells. The unique spacing of amino groups in (3S)-3,7-diaminoheptanoic acid was found to enhance peptide-membrane interactions, suggesting its potential as a scaffold for next-generation antibiotics.

Oncology applications have also emerged for this compound. Research published in Cancer Research revealed that derivatives of (3S)-3,7-diaminoheptanoic acid can selectively inhibit lysine-specific demethylase 1 (LSD1), an epigenetic regulator implicated in various cancers. The study demonstrated that these inhibitors effectively suppressed tumor growth in xenograft models while showing improved pharmacokinetic properties compared to existing LSD1 inhibitors. The compound's structural flexibility allows for optimization of both potency and selectivity against this challenging drug target.

From a drug delivery perspective, (3S)-3,7-diaminoheptanoic acid has been utilized in the development of novel polymeric carriers. A 2024 study in Advanced Materials reported pH-responsive nanoparticles incorporating this amino acid that demonstrated enhanced tumor accumulation and controlled drug release. The dual amino functionality enables precise tuning of polymer properties, including biodegradation rates and drug loading capacity, making it particularly valuable for targeted cancer therapies.

Looking forward, the versatility of (3S)-3,7-diaminoheptanoic acid positions it as a promising candidate for various biomedical applications. Ongoing research is exploring its use in mRNA delivery systems, neurodegenerative disease therapeutics, and as a component of supramolecular biomaterials. The compound's commercial availability (CAS: 13184-41-3) and improved synthetic routes are expected to accelerate its adoption in both academic and industrial research settings. Future studies will likely focus on expanding its therapeutic applications while optimizing its physicochemical properties for specific medical indications.

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