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D-Homoserine

CAS No.:
6027-21-0
Catalog Number:
AG0034P1
Molecular Formula:
C4H9NO3
Molecular Weight:
119.1192
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1g
98%
In Stock USA
United States
$28
- +
5g
95%
In Stock USA
United States
$82
- +
10g
98%
In Stock USA
United States
$138
- +
25g
95%
In Stock USA
United States
$250
- +
100g
98%
In Stock USA
United States
$725
- +
Product Description
Catalog Number:
AG0034P1
Chemical Name:
D-Homoserine
CAS Number:
6027-21-0
Molecular Formula:
C4H9NO3
Molecular Weight:
119.1192
MDL Number:
MFCD00077786
IUPAC Name:
(2R)-2-amino-4-hydroxybutanoic acid
InChI:
InChI=1S/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m1/s1
InChI Key:
UKAUYVFTDYCKQA-GSVOUGTGSA-N
SMILES:
OCC[C@H](C(=O)O)N
EC Number:
611-961-6
UNII:
5VK5MQ3TVS
Properties
Complexity:
83.4  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
119.058g/mol
Formal Charge:
0
Heavy Atom Count:
8  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
119.12g/mol
Monoisotopic Mass:
119.058g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
83.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-4.4  
Literature
Title Journal
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The Pseudomonas aeruginosa quorum-sensing signal N-(3-oxododecanoyl) homoserine lactone can accelerate cutaneous wound healing through myofibroblast differentiation in rats. FEMS immunology and medical microbiology 20110701
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Paraoxonase 2 is down-regulated by the Pseudomonas aeruginosa quorumsensing signal N-(3-oxododecanoyl)-L-homoserine lactone and attenuates oxidative stress induced by pyocyanin. The Biochemical journal 20100127
Escherichia coli autoinducer-2 uptake network does not display hysteretic behavior but AI-2 synthesis rate controls transient bifurcation. Bio Systems 20100101
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Role of PvdQ in Pseudomonas aeruginosa virulence under iron-limiting conditions. Microbiology (Reading, England) 20100101
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Genetic adaptation of Streptococcus mutans during biofilm formation on different types of surfaces. BMC microbiology 20100101
In Helicobacter pylori auto-inducer-2, but not LuxS/MccAB catalysed reverse transsulphuration, regulates motility through modulation of flagellar gene transcription. BMC microbiology 20100101
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AI-2 signalling is induced by acidic shock in probiotic strains of Lactobacillus spp. International journal of food microbiology 20091115
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Discovery of novel sphingosine kinase 1 inhibitors. Bioorganic & medicinal chemistry letters 20091101
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Differential response of Vibrio cholerae planktonic and biofilm cells to autoinducer 2 deficiency. Microbiology and immunology 20091001
Synthesis and evaluation of new antagonists of bacterial quorum sensing in Vibrio harveyi. ChemMedChem 20090901
The intrinsic reactivity of ATP and the catalytic proficiencies of kinases acting on glucose, N-acetylgalactosamine, and homoserine: a thermodynamic analysis. The Journal of biological chemistry 20090821
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Role of autoinducer-2 on the adhesion ability of Lactobacillus acidophilus. Journal of applied microbiology 20090701
Structural understanding of quorum-sensing inhibitors by molecular modeling study in Pseudomonas aeruginosa. Applied microbiology and biotechnology 20090701
Vibrio vulnificus produces quorum sensing signals of the AHL-class. FEMS microbiology ecology 20090701
Heterogeneity in quorum sensing-regulated bioluminescence of Vibrio harveyi. Molecular microbiology 20090701
Quorum quenching analysis in Pseudomonas aeruginosa and Escherichia coli: network topology and inhibition mechanism effect on the optimized inhibitor dose. Bioprocess and biosystems engineering 20090601
Pseudomonas aeruginosa Las quorum sensing autoinducer suppresses growth and biofilm production in Legionella species. Microbiology (Reading, England) 20090601
Identification and characterization of the AcrR/AcrAB system of a pathogenic Edwardsiella tarda strain. The Journal of general and applied microbiology 20090601
Exogenous Yersinia pestis quorum sensing molecules N-octanoyl-homoserine lactone and N-(3-oxooctanoyl)-homoserine lactone regulate the LcrV virulence factor. Microbial pathogenesis 20090501
Temperature, not LuxS, mediates AI-2 formation in hydrothermal habitats. FEMS microbiology ecology 20090501
Influence of Pseudomonas aeruginosa quorum sensing signal molecule N-(3-oxododecanoyl) homoserine lactone on mast cells. Medical microbiology and immunology 20090501
Biological activity and identification of a peptide inhibitor of LuxS from Streptococcus suis serotype 2. FEMS microbiology letters 20090501
Pseudomonas aeruginosa quorum-sensing signal molecules interfere with dendritic cell-induced T-cell proliferation. FEMS immunology and medical microbiology 20090401
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Quantifying the integration of quorum-sensing signals with single-cell resolution. PLoS biology 20090301
Identification, quantification, and determination of the absolute configuration of the bacterial quorum-sensing signal autoinducer-2 by gas chromatography-mass spectrometry. Chembiochem : a European journal of chemical biology 20090213
An isocratic fluorescence HPLC assay for the monitoring of l-asparaginase activity and l-asparagine depletion in children receiving E. colil-asparaginase for the treatment of acute lymphoblastic leukaemia. Biomedical chromatography : BMC 20090201
Accurate mass analysis of N-acyl-homoserine-lactones and cognate lactone-opened compounds in bacterial isolates of Pseudomonas aeruginosa PAO1 by LC-ESI-LTQ-FTICR-MS. Journal of mass spectrometry : JMS 20090201
AI-2 biosynthesis module in a magnetic nanofactory alters bacterial response via localized synthesis and delivery. Biotechnology and bioengineering 20090201
Detection of autoinducer-2 and analysis of the profile of luxS and pfs transcription in Streptococcus suis serotype 2. Current microbiology 20090201
Furanones, potential agents for preventing Staphylococcus epidermidis biofilm infections? The Journal of antimicrobial chemotherapy 20090201
The junctional integrity of epithelial cells is modulated by Pseudomonas aeruginosa quorum sensing molecule through phosphorylation-dependent mechanisms. Experimental cell research 20090115
A dynamic model for diauxic growth, overflow metabolism, and AI-2-mediated cell-cell communication of Salmonella Typhimurium based on systems biology concepts. Biotechnology and bioengineering 20090101
The luxS gene is involved in AI-2 production, pathogenicity, and some phenotypes in Erwinia amylovora. Current microbiology 20090101
[Bacterial nonpeptide quorum-sensing signal molecules]. Mikrobiologiia 20090101
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PimT, an amino acid exporter controls polyene production via secretion of the quorum sensing pimaricin-inducer PI-factor in Streptomyces natalensis. Microbial cell factories 20090101
2D proteome analysis initiates new insights on the Salmonella Typhimurium LuxS protein. BMC microbiology 20090101
AI-2 does not function as a quorum sensing molecule in Campylobacter jejuni during exponential growth in vitro. BMC microbiology 20090101
Significant immunomodulatory effects of Pseudomonas aeruginosa quorum-sensing signal molecules: possible link in human sepsis. Clinical science (London, England : 1979) 20081201
Quorum sensing in Cyanobacteria: N-octanoyl-homoserine lactone release and response, by the epilithic colonial cyanobacterium Gloeothece PCC6909. The ISME journal 20081201
Biofilm formation and autoinducer-2 signaling in Streptococcus intermedius: role of thermal and pH factors. Oral microbiology and immunology 20081201
Sinorhizobium meliloti, a bacterium lacking the autoinducer-2 (AI-2) synthase, responds to AI-2 supplied by other bacteria. Molecular microbiology 20081201
Autoinducer-2 is produced in saliva-fed flow conditions relevant to natural oral biofilms. Journal of applied microbiology 20081201
A bacterial small molecule undermining immune response signaling. Chembiochem : a European journal of chemical biology 20081103
Role of RpoS in stress survival, synthesis of extracellular autoinducer 2, and virulence in Vibrio alginolyticus. Archives of microbiology 20081101
Investigating the effect of patulin, penicillic acid and EDTA on biofilm formation of isolates from dental unit water lines. Applied microbiology and biotechnology 20081101
Directed evolution of LuxI for enhanced OHHL production. Biotechnology and bioengineering 20081001
Indole cell signaling occurs primarily at low temperatures in Escherichia coli. The ISME journal 20081001
PCR detection of Serratia spp. using primers targeting pfs and luxS genes involved in AI-2-dependent quorum sensing. Current microbiology 20081001
Enhanced biofilm formation and reduced virulence of Actinobacillus pleuropneumoniae luxS mutant. Microbial pathogenesis 20080901
Threonine biosynthetic genes are essential in Cryptococcus neoformans. Microbiology (Reading, England) 20080901
[Influence of mutations at genes of global transcriptional regulators on production of autoinducer AI-2 Quorum Sensing in the system of Escherichia coli]. Genetika 20080901
Analysis of AI-2/LuxS-dependent transcription in Campylobacter jejuni strain 81-176. Foodborne pathogens and disease 20080801
A single mutation in P450BM-3 enhances acyl homoserine lactone: acyl homoserine substrate binding selectivity nearly 250-fold. Journal of biotechnology 20080731
An unexpected switch in the modulation of AI-2-based quorum sensing discovered through synthetic 4,5-dihydroxy-2,3-pentanedione analogues. Journal of the American Chemical Society 20080723
Modulation of gene expression via disruption of NF-kappaB signaling by a bacterial small molecule. Science (New York, N.Y.) 20080711
Detection of bacterial quorum sensing N-acyl homoserine lactones in clinical samples. Analytical and bioanalytical chemistry 20080701
Regulation of autoinducer 2 production and luxS expression in a pathogenic Edwardsiella tarda strain. Microbiology (Reading, England) 20080701
Bacterial quorum sensing: a new target for anti-infective immunotherapy. Expert opinion on biological therapy 20080601
Luminescence, virulence and quorum sensing signal production by pathogenic Vibrio campbellii and Vibrio harveyi isolates. Journal of applied microbiology 20080501
Bacteriophage-amplified bioluminescent sensing of Escherichia coli O157:H7. Analytical and bioanalytical chemistry 20080501
The quorum quenching antibody RS2-1G9 protects macrophages from the cytotoxic effects of the Pseudomonas aeruginosa quorum sensing signalling molecule N-3-oxo-dodecanoyl-homoserine lactone. Molecular immunology 20080501
The Pseudomonas aeruginosa autoinducer dodecanoyl-homoserine lactone inhibits the putrescine synthesis in human cells. APMIS : acta pathologica, microbiologica, et immunologica Scandinavica 20080501
Pseudomonas aeruginosa quorum-sensing signal molecules induce IL-8 production by human corneal epithelial cells. Eye & contact lens 20080501
Raney-Co mediated reductive cyclization of an alpha,beta-unsaturated nitrile. The Journal of organic chemistry 20080418
Temporal regulation of enterohemorrhagic Escherichia coli virulence mediated by autoinducer-2. Applied microbiology and biotechnology 20080401
Autoinducer AI-2 is involved in regulating a variety of cellular processes in Salmonella Typhimurium. Foodborne pathogens and disease 20080401
Influence of autoinducer-2 (AI-2) and beef sample extracts on E. coli O157:H7 survival and gene expression of virulence genes yadK and hhA. Journal of food science 20080401
Autoinducer-2 activity of gram-negative foodborne pathogenic bacteria and its influence on biofilm formation. Journal of food science 20080401
Regulation of Vibrio alginolyticus virulence by the LuxS quorum-sensing system. Journal of fish diseases 20080301
Oxazaborolidine derivatives inducing autoinducer-2 signal transduction in Vibrio harveyi. Bioorganic & medicinal chemistry 20080215
A LuxP-based fluorescent sensor for bacterial autoinducer II. ACS chemical biology 20080215
Regulation of aspartate-derived amino acid homeostasis in potato plants (Solanum tuberosum L.) by expression of E. coli homoserine kinase. Amino acids 20080201
Stimulation of Fusobacterium nucleatum biofilm formation by Porphyromonas gingivalis. Oral microbiology and immunology 20080201
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