1186-90-9

Basic information

• Product Name: (2S,3R)-2-amino-3-hydroxy-butanedioic acid
• Synonyms: (2S,3R)-2-amino-3-hydroxy-butanedioic acid
• CAS NO: 1186-90-9
• Molecular Formula: C₄H₇NO₅
• Molecular Weight: 0
• EINECS: 224-299-4
• Mol File: 1186-90-9.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 368.7°C at 760 mmHg
• Flash Point: 176.8°C
• Appearance: /
• Density: 1.738g/cm³
• Vapor Pressure: 6.2E-07mmHg at 25°C
• Refractive Index: 1.583
• CAS DataBase Reference: (2S,3R)-2-amino-3-hydroxy-butanedioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-2-amino-3-hydroxy-butanedioic acid(1186-90-9)
• EPA Substance Registry System: (2S,3R)-2-amino-3-hydroxy-butanedioic acid(1186-90-9)

Safety Data

• Hazardous Substances Data: 1186-90-9(Hazardous Substances Data)

Usage

General Description

The chemical (2S,3R)-2-amino-3-hydroxy-butanedioic acid, also known as threonine, is an important amino acid that is used by the body to support various bodily functions. It is classified as a non-essential amino acid, which means that it is produced in the body and is also obtained through food sources such as meat, dairy, and eggs. Threonine plays a crucial role in protein synthesis, as well as in the formation of collagen and elastin, two proteins that are essential for healthy skin and connective tissue. Additionally, it contributes to the production of neurotransmitters and can support immune function. Threonine is also involved in the metabolism of fats and may have potential benefits for liver health. Overall, it is an important component of a balanced diet and is necessary for overall health and well-being.

InChI:InChI=1/C4H7NO5/c5-1(3(7)8)2(6)4(9)10/h1-2,6H,5H2,(H,7,8)(H,9,10)/t1-,2+/m0/s1

Upstream product

• 19372-03-3 aziridine-2,3-dicarboxylic acid diethyl ester 
• 16417-32-6 N-benzyl-threo-β-hydroxy-DL-aspartic acid 
• 4294-45-5 DL-threo-β-hydroxyaspartic acid 
• 1414957-69-9 taiwachelin 
• 110-17-8 (2E)-but-2-enedioic acid 
• 6463-75-8 N-(DL-α-Methyl-benzyl)-erythro-β-hydroxy-DL-asparaginsaeure 
• 2706-75-4 sodium glyoxylate 
• 7403-74-9 lower-melting inactive 3-chloro-2-hydroxy-succinic acid 
• 71653-06-0 3-hydroxyaspartic acid 
• 471242-80-5 2-amino-3-hydroxy-succinic acid dimethyl ester 
• 683228-01-5 (4R,5R)-2-Phenyl-4,5-dihydro-oxazole-4,5-dicarboxylic acid dimethyl ester 
• 403825-05-8 (2R,3R)-2-benzoylamino-3-(p-methoxy)-phenoxy-succinic acid 1-ethyl ester 4-methyl ester 
• 188530-43-0 diethyl (2R,3R)-2-hydroxy-3-aminosuccinate 

Downstream Products

• 471242-80-5 erythro-β-Hydroxy-DL-asparaginsaeuredimethylester 
• 771456-08-7 DL-erythro-3-Hydroxy-asparaginsaeure-4-methylester 
• 5753-30-0 erythro-β-hydroxy-D-aspartic acid 
• 7298-98-8 2-(S)-amino-3-(R)-hydroxysuccinic acid 
• 162553-93-7 β-Benzyl D-threo-β-hydroxyaspartate 
• 71653-06-0 3-hydroxyaspartic acid 
• 603-54-3 N,N-diphenylurea 
• 19516-01-9 (2S,3S)-2-amino-4-(benzyloxy)-3-hydroxy-4-oxobutanoic acid 
• 84035-04-1 L-threo-β-OH-Asp(OMe)-OH 
• 87-69-4 tartaric acid 
• 26462-24-8 N-Benzyloxycarbonyl-threo-hydroxy-L-aspartic acid 

Relevant articles and documents

Genomics-driven discovery of taiwachelin, a lipopeptide siderophore from Cupriavidus taiwanensis

A genome mining study led to the identification of a previously unrecognised siderophore biosynthesis gene cluster in the nitrogen-fixing bacterium Cupriavidus taiwanensis LMG19424. Based upon predicted structural residues, a convenient strategy for an NMR-assisted isolation of the associated metabolite was designed. The structure of the purified siderophore, taiwachelin, was fully characterized by spectroscopic methods and chemical derivatisation.

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Ambiguity of NRPS Structure Predictions: Four Bidentate Chelating Groups in the Siderophore Pacifibactin

Identified through a bioinformatics approach, a nonribosomal peptide synthetase gene cluster in Alcanivorax pacificus encodes the biosynthesis of the new siderophore pacifibactin. The structure of pacifibactin differs markedly from the bioinformatic prediction and contains four bidentate metal chelation sites, atypical for siderophores. Genome mining and structural characterization of pacifibactin is reported herein, as well as characterization of pacifibactin variants accessible due to a lack of adenylation domain fidelity during biosynthesis. A spectrophotometric titration of pacifibactin with Fe(III) and 13C NMR spectroscopy of the Ga(III)-pacifibactin complex establish 1:1 metal:pacifibactin coordination and reveal which of the bidentate binding groups are coordinated to the metal. The photoreaction of Fe(III)-pacifibactin, resulting from Fe(III) coordination of the β-hydroxyaspartic acid ligands, is reported.

IMPROVED RESOLUTION OF beta -HYDROXY-DL-ASPARTIC ACID ON OPTICALLY ACTIVE RESIN CONTAINING L-LYSINE OR L-ORNITHINE. erythro

A series of experiments on column chromatography of the optically active resin containing L-lysine or L-ornithine were carried out with pyridinium acetate and ammonium acetate solvent systems as the eluents. threo- beta -Hydroxy-DL-aspartic acid was found to be resolved on the optically active resin containing L-lysine with ammonium acetate solvent system; erythro- beta -hydroxy-DL-aspartic acid could be resolved on that containing L-ornithine with pyridinium acetate solvent system. The threo or erthro racemate was resolved on a preparative scale, and the resolution including the complete characterization of enantiomers resolved was first accomplished.

Stalobacin: Discovery of Novel Lipopeptide Antibiotics with Potent Antibacterial Activity against Multidrug-Resistant Bacteria

A novel lipopeptide antibiotic, stalobacin I (1), was discovered from a culture broth of an unidentified Gram-negative bacterium. Stalobacin I (1) had a unique chemical architecture composed of an upper and a lower half peptide sequence, which were linked via a hemiaminal methylene moiety. The sequence of 1 contained an unusual amino acid, carnosadine, 3,4-dihydroxyariginine, 3-hydroxyisoleucine, and 3-hydroxyaspartic acid, and a novel cyclopropyl fatty acid. The antibacterial activity of 1 against a broad range of drug-resistant Gram-positive bacteria was much stronger than those of last resort antibiotics such as vancomycin, linezolid, and telavancin (MIC 0.004-0.016 μg/mL). Furthermore, compound 1 induced a characteristic morphological change in Gram-positive and Gram-negative strains by inflating the bacterial cell body. The absolute configuration of a cyclopropyl amino acid, carnosadine, was determined by the synthetic study of its stereoisomers, which was an essential component for the strong activity of 1.