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N-3-oxo-decanoyl-L-Homoserine lactone

(Synonyms: N-(3-氧代癸酰基)-L-高丝氨酸内酯) 目录号 : GC45939

A bacterial quorum-sensing signaling molecule

N-3-oxo-decanoyl-L-Homoserine lactone Chemical Structure

Cas No.:147795-40-2

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5mg
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Sample solution is provided at 25 µL, 10mM.

Description

N-3-oxo-decanoyl-L-Homoserine lactone is a quorum-sensing signaling molecule that is produced by bacteria in response to increasing cell density.[1] It increases expression of the bacterial conjugation gene tra in A. tumefaciens in a reporter cell assay. N-3-oxo-decanoyl-L-Homoserine lactone (100 nM) induces adventitious root formation and increases expression of the auxin-response genes AUX22c and AUX22d and the cell division genes CDC2, ARC, and CDPK in mung bean seedlings.[2] It decreases expression of glucanase genes in A. thaliana when used at a concentration of 6 μM.[3]

Reference:
[1]. Zhang, L., Murphy, P.J., Kerr, A., et al. Agrobacterium conjugation and gene regulation by N-acyl-L-homoserine lactones. Nature 362(6419), 446-448 (1993).
[2]. Bai, X., Todd, C.D., Desikan, R., et al. N-3-oxo-decanoyl-L-homoserine-lactone activates auxin-induced adventitious root formation via hydrogen peroxide- and nitric oxide-dependent cyclic GMP signaling in mung bean. Plant Physiol. 158(2), 725-736 (2012).
[3]. Schenk, S.T., Hernández-Reyes, C., Samans, B., et al. N-acyl-homoserine lactone primes plants for cell wall reinforcement and induces resistance to bacterial pathogens via the salicylic acid/oxylipin pathway. Plant Cell 26(6), 2708-2723 (2014).

化学性质

Cas No. 147795-40-2 SDF
别名 N-(3-氧代癸酰基)-L-高丝氨酸内酯
化学名 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-decanamide
Canonical SMILES O=C1[C@@H](NC(CC(CCCCCCC)=O)=O)CCO1
分子式 C14H23NO4 分子量 269.3
溶解度 10mg/mL in DMSO, 30mg/mL in DMF 储存条件 Store at -20°C
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 3.7133 mL 18.5667 mL 37.1333 mL
5 mM 0.7427 mL 3.7133 mL 7.4267 mL
10 mM 0.3713 mL 1.8567 mL 3.7133 mL
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