HOMOSERINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C4H9NO3
Molecular Weight	119.1192
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@@H](CCO)C(O)=O

InChI

InChIKey=UKAUYVFTDYCKQA-VKHMYHEASA-N

InChI=1S/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C4H9NO3
Molecular Weight	119.1192
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Determination of the stoichiometry of noncovalent complexes using reverse-phase high-performance liquid chromatography coupled with electrospray ion trap mass spectrometry.	2002-10-01	12381356
Plant growth-promoting Pseudomonas putida WCS358 produces and secretes four cyclic dipeptides: cross-talk with quorum sensing bacterial sensors.	2002-10	12192521
Histidine protein kinases: key signal transducers outside the animal kingdom.	2002-09-25	12372152
Total stepwise solid-phase synthesis of oligonucleotide-(3'-->N)-peptide conjugates.	2002-09-19	12227763
Food spoilage--interactions between food spoilage bacteria.	2002-09-15	12222639
The crystal structure of the quorum sensing protein TraR bound to its autoinducer and target DNA.	2002-09-02	12198141
The Pseudomonas autoinducer N-(3-oxododecanoyl) homoserine lactone induces cyclooxygenase-2 and prostaglandin E2 production in human lung fibroblasts: implications for inflammation.	2002-09-01	12193735
The LuxR family protein SpnR functions as a negative regulator of N-acylhomoserine lactone-dependent quorum sensing in Serratia marcescens.	2002-09	12354232
Listening in on bacteria: acyl-homoserine lactone signalling.	2002-09	12209128
Biofilms: microbial life on surfaces.	2002-09	12194761
Interspecies communication between Burkholderia cepacia and Pseudomonas aeruginosa.	2002-08	12381027
Quorum sensing in plant-associated bacteria.	2002-08	12179960
Crystallization and preliminary X-ray diffraction studies of the transcriptional regulator TraR bound to its cofactor and to a specific DNA sequence.	2002-08	12136156
Effect of medium composition, flow rate, and signaling compounds on the formation of soluble extracellular materials by biofilms of Chromobacterium violaceum.	2002-07	12111158
Structure of a bacterial quorum-sensing transcription factor complexed with pheromone and DNA.	2002-06-27	12087407
Quorum sensing: an emerging target for antibacterial chemotherapy?	2002-06	12223068
Disruption of bacterial quorum sensing by other organisms.	2002-06	12180098
Can boron get bacteria talking?	2002-05	12076525
Okibacterium fritillariae gen. nov., sp. nov., a novel genus of the family Microbacteriaceae.	2002-05	12054268
Characterization of the hom-thrC-thrB cluster in aminoethoxyvinylglycine-producing Streptomyces sp. NRRL 5331.	2002-05	11988515
New synthetic analogues of N-acyl homoserine lactones as agonists or antagonists of transcriptional regulators involved in bacterial quorum sensing.	2002-04-22	11934577
Enzymatic assay of gamma-cystathionase activity using pyruvate oxidase-peroxidase sequential reaction.	2002-04-18	12062113
L-Homoserine: a novel excreted metabolic marker of hepatitis B abnormally produced in liver from methionine.	2002-04	12027520
[Synthesis of signaling N-acyl-homoserine-lactones participating in quorum sensing in rhizosphere and soil bacteria Pseudomonas and Xanthomonas].	2002-04	12018176
Cystathionine gamma-synthase and threonine synthase operate in concert to regulate carbon flow towards methionine in plants.	2002-04	11950610
Bacterial cell-to-cell communication: sorry, can't talk now - gone to lunch!	2002-04	11934621
Production and characterization of bifunctional enzymes. Domain swapping to produce new bifunctional enzymes in the aspartate pathway.	2002-03-19	11888289
Structure of the Methanococcus jannaschii mevalonate kinase, a member of the GHMP kinase superfamily.	2002-03-15	11751891
Altering plant-microbe interaction through artificially manipulating bacterial quorum sensing.	2002-03	12096736
A mathematical model of partial-thickness burn-wound infection by Pseudomonas aeruginosa: quorum sensing and the build-up to invasion.	2002-03	11926116
Detection and mutation of a luxS-encoded autoinducer in Proteus mirabilis.	2002-03	11882712
LuxS-dependent quorum sensing in Porphyromonas gingivalis modulates protease and haemagglutinin activities but is not essential for virulence.	2002-03	11882711
Detection of Pseudomonas aeruginosa cell-to-cell signals in lung tissue of cystic fibrosis patients.	2002-03	11855945
A beta-lactone route to chiral gamma-substituted alpha-amino acids: application to the concise synthesis of (S)-alpha-azidobutyro lactone and a natural amino acid.	2002-02-21	11843584
Synthesis of new 3- and 4-substituted analogues of acyl homoserine lactone quorum sensing autoinducers.	2002-02-11	11814788
A novel methodology employing Corynebacterium glutamicum genome information to generate a new L-lysine-producing mutant.	2002-02	11876415
Overproduction, purification, and characterization of recombinant bifunctional threonine-sensitive aspartate kinase-homoserine dehydrogenase from Arabidopsis thaliana.	2002-02	11812230
Structural identification of a bacterial quorum-sensing signal containing boron.	2002-01-31	11823863
Function by serendipity.	2002-01-31	11823842
Direct detection of N-acylhomoserine lactones in cystic fibrosis sputum.	2002-01-22	11886742
Characterization of N-acyl homoserine lactone overproducing mutants of Burkholderia multivorans ATCC 17616.	2002-01-10	11814664
Studies on the production of quorum-sensing signal molecules in Mannheimia haemolytica A1 and other Pasteurellaceae species.	2002-01-02	11786252
Inhibition of quorum sensing in Pseudomonas aeruginosa biofilm bacteria by a halogenated furanone compound.	2002-01	11782502
Analysis of the aspartic acid metabolic pathway using mutant genes.	2002	12083066
New homoserine lipids from Xerocomus langbianensis.	2002	11981878
Metabolic redirection of carbon flow toward isoleucine by expressing a catabolic threonine dehydratase in a threonine-overproducing Corynebacterium glutamicum.	2001-12	11778876
N-acylhomoserine-lactone-mediated communication between Pseudomonas aeruginosa and Burkholderia cepacia in mixed biofilms.	2001-12	11739757
Halogenated furanones from the red alga, Delisea pulchra, inhibit carbapenem antibiotic synthesis and exoenzyme virulence factor production in the phytopathogen Erwinia carotovora.	2001-11-27	11728727
Multidrug efflux in Pseudomonas aeruginosa: components, mechanisms and clinical significance.	2001-05	11895293
Bacterial response to siderophore and quorum-sensing chemical signals in the seawater microbial community.	2001	11716787

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:58:53 GMT 2025` Edited by `admin` on `Mon Mar 31 19:58:53 GMT 2025`
Record UNII	6KA95X0IVO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HOMOSERINE

Systematic Name

English

NSC-206251

Preferred Name

English

HOMOSERINE [MI]

Common Name

English

HOMOSERINE, L-

Systematic Name

English

L-2-AMINO-4-HYDROXYBUTYRIC ACID

Common Name

English

L-HOMOSERINE

Systematic Name

English

S-2-AMINO-4-HYDROXYBUTYRIC ACID

Common Name

English

Classification Tree Code System Code

LOINC

79631-8