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804231

2-bromo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-Benzeneacetamide

Name: 2-bromo-<I>N</I>-[(3<I>S</I>)-tetrahydro-2-oxo-3-furanyl]-Benzeneacetamide
Brand: ALDRICH

Synonym(s):

AbaR, QscR inhibitor

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About This Item

Empirical Formula (Hill Notation):

C₁₂H₁₂BrNO₃

CAS Number:

942296-18-6

Molecular Weight:

298.13

UNSPSC Code:

12352200

PubChem Substance ID:

329768854

NACRES:

NA.22

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Sigma-Aldrich

O9139

N-(3-Oxododecanoyl)-L-homoserine lactone

Sigma-Aldrich

774529

Titanium(IV) oxide

Sigma-Aldrich

O1639

N-(3-Oxooctanoyl)-DL-homoserine lactone

Sigma-Aldrich

M1434

2-Methylthioadenosine 5′-monophosphate triethylammonium salt hydrate

Sigma-Aldrich

44558

N-Octanoyl-L-homoserine lactone

Sigma-Aldrich

920479

GPhos Pd G4

Sigma-Aldrich

702668

Thieno[3,2-b]thiophene

Sigma-Aldrich

O1764

N-(3-Oxooctanoyl)-L-homoserine lactone

Sigma-Aldrich

91987

1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10-Henicosafluoro-12-iodododecane

Sigma-Aldrich

702641

Thieno[2,3-b]thiophene

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.

Pictograms

GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P301 + P312 + P330

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

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Certificates of Analysis (COA)

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Potent and selective synthetic modulators of a quorum sensing repressor in Pseudomonas aeruginosa identified from second-generation libraries of N-acylated L-homoserine lactones.

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).

Expanding dialogues: from natural autoinducers to non-natural analogues that modulate quorum sensing in Gram-negative bacteria.

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

Attenuation of quorum sensing in the pathogen Acinetobacter baumannii using non-native N-Acyl homoserine lactones.

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

Synthetic ligands that activate and inhibit a quorum-sensing regulator in Pseudomonas aeruginosa.

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

Key Documents

2-bromo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-Benzeneacetamide

About This Item

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Properties

form

storage temp.

SMILES string

InChI

InChI key

Description

Application

Safety Information

Pictograms

Signal Word

Hazard Statements

Precautionary Statements

Hazard Classifications

Storage Class Code

WGK

Flash Point(F)

Flash Point(C)

Documentation

Certificates of Analysis (COA)

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