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07077

Sigma-Aldrich

N-(p-Coumaroyl)-L-homoserine lactone

≥94% (HPLC)

Sinonimo/i:

p-Coumaroyl (S)-(−)α-amino-γ-butyrolactone, pC-HSL

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About This Item

Formula empirica (notazione di Hill):
C13H13NO4
Peso molecolare:
247.25
Numero MDL:
MFCD12912377
Codice UNSPSC:
12352209
ID PubChem:
329748342
NACRES:
NA.25

Saggio

≥94% (HPLC)

Stato

powder

Attività ottica

[α]/D -23.0±3.0°, c = 1% in ethanol

Colore

white to off-white

Punto di fusione

201.2 °C

applicazioni

cell analysis

Temperatura di conservazione

2-8°C

Stringa SMILE

Oc1ccc(\C=C\C(=O)N[C@H]2CCOC2=O)cc1
Oc1ccc(\C=C\C(=O)N[C@H]2CCOC2=O)cc1

InChI

1S/C13H13NO4/c15-10-4-1-9(2-5-10)3-6-12(16)14-11-7-8-18-13(11)17/h1-6,11,15H,7-8H2,(H,14,16)/b6-3+/t11-/m0/s1
CCIXZFJYFQJTGK-GQOHGMTASA-N

Applicazioni

N-(p-Coumaroyl)-L-homoserine lactone, or pC-HSL, can be used to study microbiology, quorum sensing and signaling compounds. pC-HSL has been used to study the activity of the Rhodopseudomonas palustris p-coumaroyl-homoserine lactone-responsive transcription factor RpaR.

Azioni biochim/fisiol

New type of bacterial, quorum sensing signal compound. Quorum sensing mechanism has been investigated in Rhodopseudomonas palustris, but the signal compound has been discovered in other bacteria such as Bradyrhizobium sp. or Silicibacter pomeroyi.

Confezionamento

Bottomless glass bottle. Contents are inside inserted fused cone.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
BCCC4076
BCBV5764
BCBP4579V
1424707V
1424707

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Hidetada Hirakawa et al.
Journal of bacteriology, 193(10), 2598-2607 (2011-03-08)
The Rhodopseudomonas palustris transcriptional regulator RpaR responds to the RpaI-synthesized quorum-sensing signal p-coumaroyl-homoserine lactone (pC-HSL). Other characterized RpaR homologs respond to fatty acyl-HSLs. We show here that RpaR functions as a transcriptional activator, which binds directly to the rpaI promoter.
Amy L Schaefer et al.
Nature, 454(7204), 595-599 (2008-06-20)
Quorum sensing is a term used to describe cell-to-cell communication that allows cell-density-dependent gene expression. Many bacteria use acyl-homoserine lactone (acyl-HSL) synthases to generate fatty acyl-HSL quorum-sensing signals, which function with signal receptors to control expression of specific genes. The
Nicolas Kylilis et al.
Nature communications, 9(1), 2677-2677 (2018-07-12)
Advancing synthetic biology to the multicellular level requires the development of multiple cell-to-cell communication channels that propagate information with minimal signal interference. The development of quorum-sensing devices, the cornerstone technology for building microbial communities with coordinated system behaviour, has largely
Sun-Young Kang et al.
Microbial cell factories, 14, 191-191 (2015-11-27)
Quorum sensing (QS) networks are more commonly known as acyl homoserine lactone (HSL) networks. Recently, p-coumaroyl-HSL has been found in a photosynthetic bacterium. p-coumaroyl-HSL is derived from a lignin monomer, p-coumaric acid, rather than a fatty acyl group. The p-coumaroyl-HSL

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