N-(beta-ketocaproyl)-L-Homoserine lactone CAS: 143537-62-6
MF: C10H15NO4
MW: 213.23
A component of quorum regulatory sensing.

N-(β-ketocaproyl)-L-Homoserine lactone (CAS 143537-62-6)

N-(β-ketocaproyl)-L-Homoserine lactone | CAS 143537-62-6 is rated 5.0 out of 5 by 1.
  • y_2022, m_8, d_15, h_22
  • bvseo_bulk, prod_bvrr, vn_bulk_3.0.32
  • cp_1, bvpage1
  • co_hasreviews, tv_0, tr_1
  • loc_en_US, sid_205396, prod, sort_[SortEntry(order=SUBMISSION_TIME, direction=DESCENDING)]
  • clientName_scbt
  • bvseo_sdk, java_sdk, bvseo-3.2.0
  • CLOUD, getAggregateRating, 113ms
  • REVIEWS, PRODUCT
loading
5
1
4
0
3
0
2
0
1
0
Alternate Names: N-(beta-Ketocaproyl)-L-homoserine lactone; N-(3-Oxohexanoyl)-L-homoserine lactone; N-(beta-Ketocaproyl)-DL-homoserine lactone
Application: N-(β-ketocaproyl)-L-Homoserine lactone is a component of quorum regulatory sensing
CAS Number: 143537-62-6
Purity: ≥95%
Molecular Weight: 213.23
Molecular Formula: C10H15NO4
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data (including water content).
loading

N-(β-ketocaproyl)-L-Homoserine lactone is a component of quorum regulatory sensing which is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). Regulation of bacterial quorum sensing signaling systems to inhibit pathogenesis represents a new approach to antimicrobial therapy in the treatment of infectious diseases. AHLs vary in acyl group length (C4-C18), in the substitution of C3 (hydrogen, hydroxyl, or oxo group), and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family. In one of the most-studied quorum-sensing systems in gram-negative bacteria, the LuxI AHL synthase catalyzes the production of N-(β-ketocaproyl)-L-homoserine lactone utilizing S-adenosylmethionine and hexanoyl-acyl carrier protein as reaction substrates in the marine bioluminescence bacterium V. fischeri. At increased populations of the bacteria, localized higher concentrations of 3-O-C6-HSL, an endogenous ligand to transcriptional factor LuxR, leads to increased production of both the AHL synthase and proteins responsible for bioluminescence. Numerous other species of bacteria also employ N-(β-ketocaproyl)-L-homoserine lactone in cell-to-cell communication.


References

1 González, J.E., Keshavan, N.D. Messing with bacterial quorum sensing. Microbiology and Molecular Biology Reviews 70(4) 859-875 (2006). 2 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). 3 Cegelski, L., Marshall, G.R., Eldridge, G.R., et al. The biology and future prospects of antivirulence therapies. Nature Reviews Microbiology 6(1) 17-27 (2008). 4 Penalver, C.G.N., Morin, D., Cantet, F., et al. Methylobacterium extorquens AM1 produces a novel type of acyl-homoserine lactone with a double unsaturated side chain under methylotrophic growth conditions. FEBS Lett 580 561-567 (2006). 5 Schaefer, A.L., Val, D.L., Hanzelka, B.L., et al. Generation of cell-to-cell signals in quorum sensing: Acyl homoserine lactone synthase activity of a purified Vibrio fischeri LuxI protien. Proc Natl Acad Sci USA 93, 9505-9509 (1996 Sep). 6 Welch, M., Todd, D.E., Whitehead, N.A., et al. N-acyl homoserine lactone binding to the CarR receptor determines quorum-sensing specificity in Erwinia. EMBO J 19(4) 631-641 (2000). 7 Ortori, C.A., Atkinson, S., Chhabra, S.R., et al. Comprehensive profiling of N-acylhomoserine lactones produced by Yersinia pseudotuberculosis using liquid chromatography coupled to hybrid quadrupole-linear ion trap mass spectrometry. Anal Bioanal Chem 387 497-511 (2007). 8 Toth, I.K., Newton, J.A., Hyman, L.J., et al. Potato plants genetically modified to produce N-acylhomoserine lactones increase susceptibility to soft rot erwiniae. Molecular Plant-Microbe Interactions 17(8) 880-887 (2004). 9 Williams, P. Quorum sensing, communication and cross-kingdom signalling in the bacterial world. Microbiology 153 3923-3938 (2007).

Physical State :
Solid
Solubility :
Soluble in ethanol, DMSO (~30 mg/ml), DMF (~30 mg/ml), methanol, and chloroform.
Storage :
Store at -20° C
Melting Point :
72-74° C
Boiling Point :
~482.9° C at 760 mmHg (Predicted)
Density :
~1.2 g/cm3 (Predicted)
Refractive Index :
n20D 1.49 (Predicted)
Optical Activity :
α20/D +5.94°, c = 0.96 in chloroform
pK Values :
pKa: 11.23 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
MDL Number :
MFCD00171363
SMILES :
CCCC(=O)CC(=O)N[[email protected]]1CCOC1=O

Download SDS (MSDS)

Certificate of Analysis

Adobe Acrobat Reader is required to reliably view,
print and comment on PDF documents

N-(beta-ketocaproyl)-L-Homoserine lactone (CAS 143537-62-6)  Product Citations

See how others have used N-(beta-ketocaproyl)-L-Homoserine lactone (CAS 143537-62-6). Click on the entry to view the PubMed entry .

Citations 1 to 2 of 2 total

PMID: # 34438972  Serrano-Aguirre, L.|Velasco-Bucheli, R.|García-Álvarez, B.|Saborido, A.|Arroyo, M.|de la Mata, I.| et al. 2021. Antibiotics (Basel). 10:

PMID: # 32313034  Nat Commun. 11: 1858.

Citations 1 to 2 of 2 total
  • bvseo_sdk, java_sdk, bvseo-3.2.0
  • CLOUD, getContent, 119ms
  • QUESTIONS, PRODUCT
  • bvseo-msg: The resource to the URL or file is currently unavailable.;
Rated 5 out of 5 by from Joshi JR; et al Joshi JR; et al. (PubMed ID: 26177258) determined that N-( -ketocaproyl)-L-Homoserine lactone decreased virulence of cinnamic acid and salicylic acid. -SCBT Publication Review
Date published: 2015-06-07
  • y_2022, m_8, d_15, h_22
  • bvseo_bulk, prod_bvrr, vn_bulk_3.0.32
  • cp_1, bvpage1
  • co_hasreviews, tv_0, tr_1
  • loc_en_US, sid_205396, prod, sort_[SortEntry(order=SUBMISSION_TIME, direction=DESCENDING)]
  • clientName_scbt
  • bvseo_sdk, java_sdk, bvseo-3.2.0
  • CLOUD, getReviews, 28ms
  • REVIEWS, PRODUCT