lhomoserine

L-Homoserine ((S)-(-)-2-AMINO-4-HYDROXYBUTYRIC ACID) 是天然存在的非蛋白丝氨酸，是合成苏氨酸、蛋氨酸和赖氨酸的共有中间体。它是氨基酸丝氨酸的更具反应性的变体。

L-Homoserine lactone is a synthetic intermediate.1,2It has been used in the synthesis of organoselenium chemistry intermediates and analogs of bacterial quorum-sensing signaling molecules. 1.Koch, T., and Buchardt, O.Synthesis of L-(+)-selenomethionineSynthesis1065-1067(1993) 2.Chhabra, S.R., Harty, C., Hooi, D.S.W., et al.Synthetic analogues of the bacterial signal (quorum seensing) molecule N-(3-oxododecanoyl)-L-homoserine lactone as immune modulatorsJ. Med. Chem.46(1)97-104(2003)

N-(beta-Ketocaproyl)-L-hoMoserine lactone (N-(Ketocaproyl)-L-homoserine lactone) 是群体调节感应的成分之一。

N-(3-hydroxy-7-cis tetradecenoyl)-L-Homoserine lactone is a long-chain N-acyl-homoserine lactone (AHL) produced by some Gram-negative bacteria and is involved in quorum sensing. Quorum sensing enables bacteria to change gene expression based on cues from nearby bacteria and from eukaryotic hosts about nutrients, environmental conditions, or threats. Due to the benefit of quorum sensing for bacterial survival, quorum sensing molecules are potential targets for controlling bacterial infections. In mouse and human leukocyte immunoassays using LPS-stimulated macrophages, N-(3-hydroxy-7-cis tetradecenoyl)-L-homoserine lactone did not have an effect on cytokine or antibody production.

O-Succinylhomoserine (O-Succinyl-L-homoserine) 是大肠杆菌合成胱硫醚的中间体。

N-Carbobenzoxy-L-homoserine (N-(Benzyloxycarbonyl)-L-homoserine) 作为一种带有 N-Carbobenzoxy保护基团的L-homoserine，常用作连接子 (ADC Linker) 以用于抗体药物偶联物 (Antibody-Drug Conjugates (ADCs)) 的合成。

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. 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. 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. C15-HSL is a product of Y. pseudituberculosis.

Quorum sensing is a regulatory process used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. 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). 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. C14:1-δ9-cis-(L)-HSL is a long-chain AHL that functions as a signaling molecule in the quorum sensing of A. vitis. Regulating bacterial quorum sensing signaling can be used to inhibit pathogenesis and thus, represents a new approach to antimicrobial therpy in the treatment of infectious diseases.

N-Heptanoyl-L-homoserine lactone 在生命科学相关研究中具有广泛的应用。

N-(3-Oxodecanoyl)-L-homoserine lactone (3-Oxo-C10-HSL) 作为一种信号分子，在细菌群体感应中充当自诱导分子的角色。

N-phenylacetyl-L-Homoserine lactone 可衰减病原体鲍曼不动杆菌的群体感应，可用于研究细菌感染。

N-butyryl-L-Homoserine lactone-d5,是N-Butanoyl-L-homoserine lactone的一个同位素标记版本,含有五个氘原子.该化合物作为一种可降解的ADC linker,主要在抗体偶联活性分子(ADCs)的合成中使用.此外,N-Butanoyl-L-homoserine lactone还展示出抗菌活性,并可应用于抗菌生物膜的研发.它的适配体还具有阻断群体感应的能力,可以有效抑制铜绿假单胞菌(Pseudomonas aeruginosa)生物膜的形成.

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by the synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-3-oxo-tetradecanoyl-L-homoserine lactone (3-oxo-C14-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria.[1] [2] [3] It appears later than shorter acyl chain AHLs in developing biofilms [4] and, like other long chain 3-oxo-AHLs, stimulates the production of putisolvin, [5] which in turn, inhibits biofilm formation.

Quorum sensing is a regulatory process used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. 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). 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. C18:1-δ9 cis-(L)-HSL is a long-chain AHL that may have antimicrobial activity and thus, might be used to inhibit pathogenesis by regulating bacerial quorum sensing signaling.

N-(Ketocaproyl)-DL-homoserine lactone 是群体感应自动诱导剂。它是 LuxR 的天然配体。

Quorum sensing is a regulatory process 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). 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.[3] C16:1-Δ9-(L)-HSL is a long-chain AHL that functions as a quorum sensing signaling molecule in strains of S. meliloti.[4],[5],[6],[7] Regulating bacterial quorum sensing signaling can be used to inhibit pathogenesis and thus, represents a new approach to antimicrobial therapy in the treatment of infectious diseases.[8] Reference：[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]. 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(2), 561-567 (2006).[4]. 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. Archives of Microbiology 180, 494-497 (2003).[5]. Gao, M., Chen, H., Eberhard, A., et al. sinI- and expR-dependent quorum sensing in Sinorhizobium meliloti. Journal of Bacteriology 187(23), 7931-7944 (2005).[6]. Marketon, M.M., Glenn, S.A., Eberhard, A., et al. Quorum sensing controls exopolysaccharide production in Sinorhizobium meliloti. Journal of Bacteriology 185(1), 325-331 (2003).[7]. Marketon, M., Gronquist, M.R., Eberhard, A., et al. Characterization of the Sinorhizobium meliloti sinR sinI locus and the production of novel N-Acyl homoserine lactones. Journal of Bacteriology 184(20), 5686-5695 (2002).[8]. 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).

N-3-oxo-dodecanoyl-L-Homoserine lactone (3-oxo-C12-HSL) 是由铜绿假单胞菌和洋葱状芽孢杆菌复合物菌株产生的细菌群体感应信号分子，群体感应是细菌用来控制基因表达以响应细胞密度增加的调节系统。N-3-oxo-dodecanoyl-L-Homoserine lactone 诱导 16HBE 人支气管上皮细胞产生 IL-8。

N-octanoyl-L-Homoserine lactone (C8-HSL) 是一种具有扩散性的外源性鼠疫耶尔森菌群体感应分子，可调节LcrV毒力因子，通过参与群体感应控制基因表达，影响细胞代谢。N-octanoyl-L-Homoserine lactone 是用于研究囊性纤维的感染。

N-decanoyl-L-Homoserine lactone (C10-HSL) 是一种由克雷莫里色假单胞菌菌株 ND07产生的 N-acyl-homoserine lactone (AHL)。N-decanoyl-L-homoserine lactone 可抑制拟南芥的主根生长。N-decanoyl-L-homoserine lactone 处理可引起拟南芥根胞质游离 Ca2+ 和活性氧 (ROS) 浓度短暂和和立即升高，增加丝裂原激活蛋白激酶 6 (MPK6) 的活性，并促使一氧化氮 (NO) 的产生。

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. 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. 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. N-tridecanoyl-L-Homoserine lactone (C13-HSL) possesses a rare odd-numbered acyl carbon chain and is produced by wild-type and mutant strains of Y. pseudotuberculosis in trace amounts.

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. 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. 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. C11-HSL possesses a rare odd-numbered acyl carbon chain and may be a minor quorum-sensing signaling molecule in P. aeruginosa strains.

N-hexanoyl-DL-Homoserine lactone (C6-HSL) 是从双壳类幼虫培养物中分离出来的，可降解细菌，可抑制植物病原真菌 B. cinerea 诱导的病变。N-hexanoyl-DL-Homoserine lactone 参与细菌间的N-酰基-高丝氨酸内酯 （AHL） 群体感应 （QS） 系统。

N-3-hydroxyoctanoyl-L-Homoserine lactone, a small diffusible signaling molecule secreted by various bacteria, plays a critical role in quorum sensing—a regulatory system used by bacteria to control gene expression according to cell density changes. This compound is generated via lactonolysis from 3-oxooctanoyl-homoserine lactone and can either activate or suppress gene expression and biofilm formation. Its production and function vary within the bacterial population growth phases, consequently mediating distinct cellular effects through alterations in gene expression, hence contributing to either quorum sensing or quenching.

N-3-hydroxydecanoyl-DL-Homoserine lactone is a bacterial quorum-sensing molecule.1It activates SdiA (EC50= 0.6 μM), a transcription factor that detects N-acyl homoserine lactones (AHLs), in the 14028 pJNS25 strain ofS. enterica.2 1.Fekete, A., Frommberger, M., Rothballer, M., et al.Identification of bacterial N-acylhomoserine lactones (AHLs) with a combination of ultra-performance liquid chromatography (UPLC), ultra-high-resolution mass spectrometry, and in-situ biosensorsAnal. Bioanal. Chem.387455-467(2007) 2.Janssens, J.C.A., Metzger, K., Daniels, R., et al.Synthesis of N-acyl homoserine lactone analogues reveals strong activators of SdiA, the Salmonella enterica serovar Typhimurium LuxR homologueAppl. Environ. Microb.73(2)535-544(2007)