A C2 N-acyl homoserine lactone
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Product Categories

Product Type

Biochemicals
Homoserine Lactones

Research Area

Acetyl-L-Homoserine lactone

Item No. 23241

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(3S)-tetrahydro-2-oxo-3-furanyl]-acetamide
CAS Number
51524-71-1
Synonyms
  • Acetyl-L-HSL
  • C2-HSL
Molecular Formula
C6H9NO3
Formula Weight
143.1
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: Soluble
SMILES
O=C1OCC[C@@H]1NC(C)=O
InChi Code
InChI=1S/C6H9NO3/c1-4(8)7-5-2-3-10-6(5)9/h5H,2-3H2,1H3,(H,7,8)/t5-/m0/s1
InChi Key
XGSXMDQVYYCSDA-YFKPBYRVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $81

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    10 mg

    $152

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    25 mg

    $357

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    Product Description

    Acetyl-L-homoserine lactone belongs to the family of N-acylated homoserine lactones (HSLs) and has an acyl chain length of two carbons.1 HSLs perform a role in quorum sensing; however, unlike other HSLs, acetyl-L-homoserine lactone does not elicit a response in bacteria. In an assay of carbapenem antibiotic biosynthesis, acetyl-L-homoserine lactone does not induce a response in E. carotovora.2 In a fluorescence assay using E. coli containing a reporter plasmid of GFP expression in response to exogenous HSLs, acetyl-L-homoserine does not elicit GFP production.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. González, J.E., and Keshavan, N.D. Messing with bacterial quorum sensing. Microbiol. Mol. Biol. Rev. 70(4), 859-875 (2006).

    2. Chhabra, S.R., Stead, P., Bainton, N.J., et al. Autoregulation of carbapenem biosynthesis in Erwinia carotovora by analogues of N-(3-oxohexanoyl)-L-homoserine lactone. J. Antibiot. (Tokyo) 46(3), 441-454 (1993).

    3. Syrpas, M., Ruysbergh, E., Blommaert, L., et al. Haloperoxidase mediated quorum quenching by Nitzschia cf pellucida: Study of the metabolization of N-acyl homoserine lactones by a benthic diatom. Mar. Drugs 12(1), 352-367 (2014).

    Product Citations

    Pundir, P., Liu, R., Vasavda, C., et al. A connective tissue mast-cell-specific receptor detects bacterial quorum-sensing molecules and mediates antibacterial immunity. Cell Host Microbe 26, 114-122 (2019).