51524-71-1

Basic information

• Product Name: C2-HSL, N-Acetyl-L-hoMoserine lactone
• Synonyms: Acetyl-L-hoMoserine lactone;C2-HSL, N-Acetyl-L-hoMoserine lactone
• CAS NO: 51524-71-1
• Molecular Formula: C₆H₉NO₃
• Molecular Weight: 173.12348
• Mol File: 51524-71-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 82-84 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• Boiling Point: 441.3±34.0 °C(Predicted)
• Appearance: /
• Density: 1.20±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMF (Sparingly), Methanol (Slightly, Sonicated)
• PKA: 14.78±0.20(Predicted)
• CAS DataBase Reference: C2-HSL, N-Acetyl-L-hoMoserine lactone(CAS DataBase Reference)
• NIST Chemistry Reference: C2-HSL, N-Acetyl-L-hoMoserine lactone(51524-71-1)
• EPA Substance Registry System: C2-HSL, N-Acetyl-L-hoMoserine lactone(51524-71-1)

Safety Data

• Hazardous Substances Data: 51524-71-1(Hazardous Substances Data)

Usage

Description

Acetyl-L-homoserine lactone belongs to the family of N-acylated homoserine lactones (HSLs) and has an acyl chain length of two carbons. HSLs perform a role in quorum sensing; however, unlike other HSLs, acetyl-L-homoserine lactone does not elicit a response in bacteria. In an assay of carbapenem antibiotic biosynthesis, acetyl-L-homoserine lactone does not induce a response in E. carotovora. In a fluorescence assay using E. coli containing a reporter plasmid of GFP expression in response to exogenous HSLs, acetyl-L-homoserine does not elicit GFP production.

Uses

Acetyl-L-homoserine lactone is the shortest alkyl homologue and most polar of a family of mediators of cel- t- cell interactions in bacterial biofilms. Acylhomoserine lactones have been detected in hundreds of bacterial species and, while the homologues vary between species and strains, the homoserine lactones are the major chemical modulators of within and between cell communication and regulation. Acetyl-L-homoserine lactone is not found in nature and can serve as a polar negative control for quorum sensing events.

Upstream product

• 7540-67-2 O-acetyl-L-homoserine 
• 108-24-7 acetic anhydride 
• 77856-40-7 (S)-2-oxotetrahydrofuran-3-aminium trifluoroacetate 
• 914306-13-1 C₇H₁₃NO₄ 
• 6305-38-0 (S)-(-)-α-amino-γ-butyrolactone hydrobromide 
• 75-36-5 acetyl chloride 
• 672-15-1 L-homoserine 

Downstream Products

• 65-82-7 N-acetyl-l-methionine 
• 1195-16-0 N-acetyl-DL-homocysteinethiolactone 

Relevant articles and documents

1,5-Asymmetric induction in reactions between 4- and 5-alkoxypent-2-enyl(tributyl)stannanes and achiral 1-alkoxycarbonylimines

Tin(IV) chloride promoted reactions of 4- and 5-alkoxypent-2-enyl(tributyl)stannanes 1, 11 and 15 and 1-alkoxycarbonylimines 2 proceed with excellent 1,5-asymmetric induction.

Solution structural features of N-acyl homoserine lactones

Here we demonstrate that in interbacterial quorum signal moderators, N-acylhomoserine lactones (AHLs), the stabilization of bioactive pharmacophore lactone against lysis is through the e- withdrawing N-acyl motif which reduces lactone carbonyl polarization. This lysis is assisted by weak (-1) contacts between N-acyl O and lactone C′. The interactions that preclude this weak contact, in the free and receptor-bound AHLs, improve lactone halflife and hence are key to the design of the antibacterial AHL analogues.

Remote stereocontrol in reactions between 4- and 5-alkoxyalk-2- enylstannanes and 1-alkoxycarbonylimines and analogues: Stereoselective approaches to novel α-amino acids

Reactions of the allyltin trichloride 45 generated from (4S)-4-benzyloxypent-2-enyl(tributyl)stannane 1 with imines prepared from glyoxylates proceed with useful levels of 1,5-stereocontrol in favour of (4E)-2,6-anti-2-(alkylamino)-6-benzyloxyhept-4-enoat