See personalized New Product recommendations! Get personalized New Product recommendations! Register or Login for personalized New Product recommendations!

Holiday Notification: Cayman Chemical will be closed Monday, May 28, 2012, in observance of the Memorial Day holiday. More…
Please feel free to continue placing orders via our website or via fax at 734-971-3640. You may send an email to customer service at custserv@caymanchem.com , or to technical support at techserv@caymanchem.com which we will respond to the next business day. Cayman will resume regular business hours and shipping schedules on Tuesday, May 29, 2012. Thank you for your patience and understanding.

N-hexadecanoyl-L-Homoserine lactone

Cayman Chemical Item Number 13064

C16-HSL; N-palmitoyl-L-Homoserine (CAS 87206-01-7)

N-hexadecanoyl-L-Homoserine lactone (CAS 87206-01-7)

See more

Description

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density.1 This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production.2 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.3 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.4 C16-HSL is one of a number of lipophilic, long acyl side-chain bearing AHLs, including its monounsaturated analog C16:1-(L)-HSL, produced by the LuxI AHL synthase homolog SinI involved in quorum-sensing signaling in S. meliloti, a nitrogen-fixing bacterial symbiont of certain legumes.5,6 C16-HSL is the most abundant AHL produced by the proteobacterium R. capsulatus and activates genetic exchange between R. capsulatus cells.7 N-Hexadecanoyl-L-homoserine lactone and other hydrophobic AHLs tend to localize in relatively lipophilic cellular environments of bacteria and cannot diffuse freely through the cell membrane. The long-chain N-acylhomoserine lactones may be exported from cells by efflux pumps or may be transported between communicating cells by way of extracellular outer membrane vesicles.8,9

1 González, J.E., and Keshavan, N.D. Messing with bacterial quorum sensing. Microbiol Mol Biol Rev 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. Nat Rev Microbiol 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 Gao, M., Chen, H., Eberhard, A., et al. sinI- and expR-dependent quorum sensing in Sinorhizobium meliloti. J Bacteriol 187(23) 7931-7944 (2005).

6 Teplitski, M., Eberhard, A., Gronquist, M.R., et al. Chemical identification of N-acyl homoserine lactone quorum-sensing signals produced by Sinorhizobium meliloti strains in defined medium. Arch Microbiol 180 494-497 (2003).

7 Schaefer, A.L., Taylor, T.A., Beatty, J.T., et al. Long-chain acyl-homoserine lactone quorum-sensing regulation of Rhodobacter capsulatus gene transfer agent production. J Bacteriol 184(23) 6515-6521 (2002).

8 Pearson, J.P., Van Delden, C., and Iglewski, B.H. Active efflux and diffusion are involved in transport of Pseudomonas aeruginosa cell-to-cell signals. J Bacteriol 181(4) 1203-1210 (1999).

9 Mashburn-Warren, L., and Whiteley, M. Special delivery: Vesicle trafficking in prokaryotes. Mol Microbiol 61(4) 839-846 (2006).

Synonyms
  • C16-HSL
  • N-palmitoyl-L-Homoserine
Formal Name N-​[(3S)-​tetrahydro-​2-​oxo-​3-​furanyl]-​hexadecanamide
CAS Number 87206-01-7
Molecular Formula C20H37NO3
Formula Weight 339.5
Formulation A crystalline solid
Purity ≥95%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CCCCCCCCCCCCCCCC(=O)​N[C@H]​1CCOC1=O

Background Reading

Pearson, J.P., Van Delden, C., and Iglewski, B.H. Active efflux and diffusion are involved in transport of Pseudomonas aeruginosa cell-to-cell signals. J Bacteriol 181(4) 1203-1210 (1999).

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).

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).

Teplitski, M., Eberhard, A., Gronquist, M.R., et al. Chemical identification of N-acyl homoserine lactone quorum-sensing signals produced by Sinorhizobium meliloti strains in defined medium. Arch Microbiol 180 494-497 (2003).

Cegelski, L., Marshall, G.R., Eldridge, G.R., et al. The biology and future prospects of antivirulence therapies. Nat Rev Microbiol 6(1) 17-27 (2008).

Gao, M., Chen, H., Eberhard, A., et al. sinI- and expR-dependent quorum sensing in Sinorhizobium meliloti. J Bacteriol 187(23) 7931-7944 (2005).

Schaefer, A.L., Taylor, T.A., Beatty, J.T., et al. Long-chain acyl-homoserine lactone quorum-sensing regulation of Rhodobacter capsulatus gene transfer agent production. J Bacteriol 184(23) 6515-6521 (2002).

González, J.E., and Keshavan, N.D. Messing with bacterial quorum sensing. Microbiol Mol Biol Rev 70(4) 859-875 (2006).

Mashburn-Warren, L., and Whiteley, M. Special delivery: Vesicle trafficking in prokaryotes. Mol Microbiol 61(4) 839-846 (2006).

Krick, A., Kehraus, S., Eberl, L., et al. A marine Mesorhizobium sp. Produces structurally novel long-chain N-acyl-L-homoserine lactones. Appl Environ Microbiol 73(11) 3587-3594 (2007).

Show all 10 Hide all but first 3

N-hexadecanoyl-L-Homoserine lactone is available in the following screening library:

Size Price Quantity Subtotal
5 mg $30.00 $0.00
10 mg $57.00 $0.00
25 mg $135.00 $0.00
50 mg $240.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-26. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

N-3-hydroxydecanoyl-L-Homoserine lactone New Exclusive
N-3-hydroxyoctanoyl-L-Homoserine lactone New Exclusive
N-3-oxo-dodecanoyl-L-Homoserine lactone
N-butyryl-L-Homoserine lactone
N-cis-hexadec-9Z-enoyl-L-Homoserine lactone Exclusive
N-cis-octadec-9Z-enoyl-L-Homoserine lactone Exclusive
N-cis-tetradec-9Z-enoyl-L-Homoserine lactone Exclusive
N-hexanoyl-L-Homoserine lactone
N-(β-ketocaproyl)-L-Homoserine lactone
Show all 9 Hide all but first 3

Downloads

Batch-specific Information

Login to access batch-specific information

Cayman Chemical is a manufacturer, supplier and vendor of biochemical reagents, assay kits, antibodies, and proteins.

Other Resources
Management Team Company Profile Company History ChemAssistant Tools FAQs Cayman Europe Cayman Pharma CaBRI Cayman Gear Press Releases Illustrations and Charts Key Research Area Posters Article Library Analysis Tools Conference Schedule Order Terms Browser Recommendation Privacy Statement Site Map

Cayman Chemical Company · 1180 East Ellsworth Road · Ann Arbor, Michigan 48108 · USA

Toll Free: (800) 364-9897 (USA and Canada Only) · Fax: (734) 971-3640

Copyright 2012 Cayman Chemical Company

Lost password?