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

Description

(2S,3R)-2-amino-3-hydroxy-butanedioic acid, also known as threonine, is an essential amino acid that plays a vital role in various bodily functions. It is classified as a non-essential amino acid, which means that it is produced in the body and can also be obtained through food sources such as meat, dairy, and eggs. Threonine is crucial for protein synthesis, collagen and elastin formation, neurotransmitter production, immune function, and fat metabolism, making it an important component of a balanced diet for overall health and well-being.

Uses

Used in Nutritional Supplements:
(2S,3R)-2-amino-3-hydroxy-butanedioic acid is used as a nutritional supplement to support overall health and well-being. It helps in protein synthesis, which is essential for muscle growth and repair, and contributes to the formation of collagen and elastin, promoting healthy skin and connective tissue.
Used in Skincare Products:
(2S,3R)-2-amino-3-hydroxy-butanedioic acid is used as an ingredient in skincare products for its role in collagen and elastin formation. It helps maintain skin elasticity and suppleness, reducing the appearance of wrinkles and fine lines.
Used in Pharmaceutical Industry:
(2S,3R)-2-amino-3-hydroxy-butanedioic acid is used in the pharmaceutical industry for its potential benefits in liver health and immune function. It may be included in formulations to support liver health and enhance immune response.
Used in Food and Beverage Industry:
(2S,3R)-2-amino-3-hydroxy-butanedioic acid is used as a food additive to enhance the nutritional value of various products. It can be added to protein-rich foods, such as meat, dairy, and eggs, to increase their amino acid content and support overall health.
Used in Research and Development:
(2S,3R)-2-amino-3-hydroxy-butanedioic acid is used in research and development for its potential applications in various fields, such as pharmaceuticals, nutraceuticals, and cosmetics. It is studied for its role in protein synthesis, neurotransmitter production, and other biological processes to develop new products and therapies.

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

• 141-36-6 DL-trans-epoxysuccinic acid 
• 4294-45-5 DL-threo-β-hydroxyaspartic acid 
• 152698-53-8 (2S,3S)-dimethyl 3-hydroxy-N-benzyloxycarbonyl-L-aspartate 
• 683228-02-6 (4S,5S)-2-Methyl-4,5-dihydro-oxazole-4,5-dicarboxylic acid dimethyl ester 
• 7440-44-0 pyrographite 
• 17015-08-6 (2R,3R)-oxirane-2,3-dicarboxylic acid 
• 71653-06-0 3-hydroxyaspartic acid 
• 16417-32-6 N-benzyl-threo-β-hydroxy-DL-aspartic acid 
• 19372-03-3 aziridine-2,3-dicarboxylic acid diethyl ester 
• 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 
• 471242-80-5 2-amino-3-hydroxy-succinic acid dimethyl ester 

Downstream Products

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

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.