804231
2-bromo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-Benzeneacetamide
Synonym(s):
AbaR, QscR inhibitor
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About This Item
Empirical Formula (Hill Notation):
C12H12BrNO3
CAS Number:
Molecular Weight:
298.13
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.22
form
solid
storage temp.
−20°C
SMILES string
O=C(OCC1)[C@@]1([H])NC(CC2=C(Br)C=CC=C2)=O
InChI
1S/C12H12BrNO3/c13-9-4-2-1-3-8(9)7-11(15)14-10-5-6-17-12(10)16/h1-4,10H,5-7H2,(H,14,15)/t10-/m0/s1
InChI key
MMJSTOMMZPSKSQ-JTQLQIEISA-N
Application
The following AHL is a phenylacetanoyl L-homoserine lactone (PHL), a class of compounds found to strongly modulate many LuxR-type receptors. It is an active inhibitor of the putative LuxR-type receptor in Acinetobacter baumannii – AbaR and the quorum-sensing repressor in P. aeruginosa – QscR.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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Margrith E Mattmann et al.
Chembiochem : a European journal of chemical biology, 12(6), 942-949 (2011-03-03)
Bacteria can coordinate group behavior using chemical signals in a process called quorum sensing (QS). The QS system in the opportunistic pathogen Pseudomonas aeruginosa is largely governed by the LasR receptor and its cognate chemical signal, N-(3-oxo)-dodecanoyl L-homoserine lactone (OdDHL).
Grant D Geske et al.
Chemical Society reviews, 37(7), 1432-1447 (2008-06-24)
Bacteria are capable of "communicating" their local population densities via a process termed quorum sensing (QS). Gram-negative bacteria use N-acylated l-homoserine lactones (AHLs), in conjunction with their cognate LuxR-type receptors, as their primary signalling circuit for QS. In this critical
Danielle M Stacy et al.
ACS chemical biology, 7(10), 1719-1728 (2012-08-03)
Many bacterial pathogens use quorum sensing (QS) to control virulence. As a result, the development of methods to intercept QS has attracted significant interest as a potential anti-infective therapy. Acinetobacter baumannii has emerged as a pan-drug-resistant pathogen and displays a
Margrith E Mattmann et al.
Bioorganic & medicinal chemistry letters, 18(10), 3072-3075 (2007-12-18)
The transcription factor QscR is a regulator of quorum sensing in Pseudomonas aeruginosa and plays a role in controlling virulence in this prevalent opportunistic pathogen. This study outlines the discovery of a set of synthetic N-acylated homoserine lactones that are
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