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804258

Sigma-Aldrich

N-(3-(4-bromophenyl)-propanoyl)-L-homoserine lactone

≥95%

Synonym(s):

4-bromo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-benzenepropanamide, LasR and TraR inhibitor, LuxR

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About This Item

Empirical Formula (Hill Notation):
C13H14BrNO3
CAS Number:
959613-39-9
Molecular Weight:
312.16
UNSPSC Code:
12352200
PubChem Substance ID:
329768855
NACRES:
NA.22

Assay

≥95%

form

solid

storage temp.

−20°C

SMILES string

O=C(OCC1)[C@@]1([H])NC(CCC2=CC=C(Br)C=C2)=O

InChI

1S/C13H14BrNO3/c14-10-4-1-9(2-5-10)3-6-12(16)15-11-7-8-18-13(11)17/h1-2,4-5,11H,3,6-8H2,(H,15,16)/t11-/m0/s1

InChI key

SGDZSJUYCLTPRG-NSHDSACASA-N

Application

AHL analog is a strong, broad-spectrum inhibitor of numerous LuxR-type receptors (e.g.: LuxR from Vibrio fischeri, LasR from P. aeruginosa, and TraR from Agrobacterium tumefaciens). This compound represents a good choice for initial testing of LuxR-type receptor inhibition.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Grant D Geske et al.
Chembiochem : a European journal of chemical biology, 9(3), 389-400 (2008-01-29)
Bacterial quorum sensing is mediated by low molecular-weight signals and plays a critical role in both the pathogenesis of infectious disease and beneficial symbioses. There is significant interest in the development of synthetic ligands that can intercept bacterial quorum sensing
Grant D Geske et al.
Journal of the American Chemical Society, 129(44), 13613-13625 (2007-10-12)
Bacteria use a language of low molecular weight ligands to assess their population densities in a process called quorum sensing. This chemical signaling process plays a pivotal role both in the pathogenesis of infectious disease and in beneficial symbioses. There

Articles

Quorum Sensing Modulators

Quorum sensing is a chemical communication mechanism used by many common bacteria to initiate group behaviors. It plays an important role in the establishment of infection by pathogens and in mediating certain symbioses.

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