An internal standard for the quantification of N-hexanoyl-L-homoserine lactone
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Unlabeled Version(s)
10007896N-hexanoyl-L-Homoserine lactone
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N-hexanoyl-L-Homoserine lactone-d3

Item No. 10007897

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(3S)-tetrahydro-2-oxo-3-furanyl]-hexanamide-6,6,6-d3
CAS Number
2705226-73-7
Synonyms
  • C6-HSL-d3
Molecular Formula
C10H14D3NO3
Formula Weight
202.3
Purity
≥99% deuterated forms (d1-d3)
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
O=C1[C@@H](NC(CCCCC([2H])([2H])[2H])=O)CCO1
InChi Code
InChI=1S/C10H17NO3/c1-2-3-4-5-9(12)11-8-6-7-14-10(8)13/h8H,2-7H2,1H3,(H,11,12)/t8-/m0/s1/i1D3
InChi Key
ZJFKKPDLNLCPNP-TUWYYBGVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

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    Product Description

    N-hexanoyl-L-Homoserine lactone-d3 (C6-HSL-d3) contains three deuterium atoms at the C-6 position. It is intended for use as an internal standard for the quantification of C6-HSL by GC- or LC-mass spectrometry. Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. A promising field of study involves controlling bacterial infections by quenching their quorum sensing systems. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by synthesis of diffusible acylhomoserine lactone (AHL) molecules. C6-HSL is a small diffusible signaling molecule involved in quorum sensing, controlling gene expression, and affecting cellular metabolism.1 The diverse applications of this molecule include regulation of virulence in general and in cystic fibrosis, infection prevention, slime and biofilm reduction in commercial agriculture and aquaculture industries, food spoilage prevention, and septicemia in fish.2,3,4,5,6,7,8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gould, T.A., Herman, J., Krank, J., et al. Specificity of acyl-homoserine lactone syntheses examined by mass spectrometry. J. Bacteriol. 188(2), 773-783 (2006).

    2. Morohoshi, T., Inaba, T., Kato, N., et al. Identification of quorum-sensing signal molecules and the LuxRI homologs in fish pathogen Edwardsiella tarda. J. Biosci. Bioeng. 98(4), 274-281 (2004).

    3. Ulrich, R.L., Hines, H.B., Parthasarathy, N., et al. Mutational analysis and biochemical characterization of the bukholderia thailandensis DW503 quorum-sensing network. J. Bacteriol. 186(13), 4350-4360 (2004).

    4. Wang, L.H., Weng, L.X., Dong, Y.H., et al. Specificity and enzyme kinetics of the quorum-quenching N-acyl homoserine lactone lactonase (AHL-lactonase). The Journal of Biological Chemisty 279(14), 13645-13651 (2004).

    5. Yates, E.A., Philipp, B., Buckley, C., et al. N-acylhomoserine lactones undergo lactonolysis in a pH-temperature-, and acyl chain length-dependent manner during growth of yersinia pseudotuberculosis and pseudomonas aeruginosa. Infect. Immun. 70(10), 5635-5646 (2002).

    6. Luo, Z.Q., Su, S., and Farrand, S.K. In situ activation of the quorum-sensing transcription factor TraR by cognate and noncognate acyl-homoserine lactone ligands: Kinetics and consequences. J. Bacteriol. 186(19), 5665-5672 (2003).

    7. Christensen, A.B., Riedel, K., Eberl, L., et al. Quorum-sensing-directed protein expression in Serratia proteamaculans B5a. Microbiology 149(Pt 2), 471-483 (2003).

    8. Chambers, C.E., Visser, M.B., Schwab, U., et al. Identification of N-acylhomoserine lactones in mucopurulent respiratory secretions from cystic fibrosis patients. FEMS Microbiol. Lett. 244(2), 297-304 (2005).