28954-12-3

Basic information

• Product Name: L(+)-allo-Threonine
• Synonyms: l-allothreonin;O-T-BUTYL-L-ALLO-THREONINE;H-ALLO-THR(BUT)-OH;H-ALLO-THR-O;H-ALLO-THR-OH;H-ALLO-THR(TBU)-OH;H-L-ALLO-THR-OH;L(+)-ALLO-THREONINE
• CAS NO: 28954-12-3
• Molecular Formula: C₄H₉NO₃
• Molecular Weight: 119.12
• EINECS: 249-327-2
• Product Categories: Threonine [Thr, T];Amino Acids;amino acid derivative
• Mol File: 28954-12-3.mol

Chemical Properties

• Melting Point: 272 °C (dec.)(lit.)
• Boiling Point: 222.38°C (rough estimate)
• Flash Point: 162.9 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.3126 (rough estimate)
• Refractive Index: 10 ° (C=5, H2O)
• Storage Temp.: Store at RT.
• Solubility: Water (Slightly)
• PKA: pK1: 2.108(+1);pK2: 9.096(0) (25°C)
• BRN: 1721645
• CAS DataBase Reference: L(+)-allo-Threonine(CAS DataBase Reference)
• NIST Chemistry Reference: L(+)-allo-Threonine(28954-12-3)
• EPA Substance Registry System: L(+)-allo-Threonine(28954-12-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: BA4055000
• Hazardous Substances Data: 28954-12-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L(+)-allo-Threonine is used as a reactant for the synthesis of specific antibiotics, such as globomycin and its congener, SF-1902 A5. These antibiotics are employed to treat various bacterial infections, highlighting the importance of L(+)-allo-Threonine in the development of pharmaceutical compounds.
In the synthesis of these antibiotics, L(+)-allo-Threonine serves as a crucial building block, contributing to the overall structure and function of the final product. Its unique properties allow for the creation of antibiotics with specific modes of action, targeting and eliminating harmful bacteria effectively.
Overall, L(+)-allo-Threonine is a valuable compound in the pharmaceutical industry, playing a vital role in the development and synthesis of antibiotics that help combat bacterial infections and improve public health.

InChI:InChI=1/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3-/m0/s1

Upstream product

• 72-19-5 rac-allo-threonine 
• 157458-06-5 (4S,5S)-2-(3,4-Dihydroxybenzoyl)-5-methyl-2-oxazoline-4-carboxylic acid 
• 7732-18-5 water 
• 66-72-8 pyridoxal 
• 75-07-0 acetaldehyde 
• 56-40-6 glycine 
• 5431-93-6 ethyl 2-(acetylamino)-3-oxobutanoate 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 
• 66508-93-8 ethyl 2-(hydroxyimino)-3-oxybutyrate 
• 108-24-7 acetic anhydride 
• 82659-84-5 (4S,5S)-5-methyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 115527-74-7 (2S,3S)-methyl-N-trifluoroacetyl-O-(m-chlorobenzoyl)-threoninate 
• 84500-44-7 ethyl (2S)-3-hydroxy-2-tert-butylcarbonylaminobutanoate 

Downstream Products

• 39994-75-7 (+/-) threonine methyl ester hydrochloride 
• 7537-02-2 threonine TMS 
• 56884-52-7 1-[6-anilino-5-hydroxy-2-(1-hydroxy-ethyl)-benzooxazol-4-yl]-ethanone 
• 13881-40-8 2-Brom-3-hydroxy-buttersaeure 
• 3913-65-3 2-hydroxypropanal 
• 72-19-5 L-threonine 
• 72-19-5 D-threonine 
• 138-15-8 l-glutamic acid hydrochloride 
• 617-61-8 D-glutamic acid hydrochloride 
• 600-18-0 2-Oxobutyric acid 
• 7664-41-7 ammonia 
• 75-07-0 acetaldehyde 
• 56-40-6 glycine 
• 124-38-9 carbon dioxide 

Relevant articles and documents

Noncovalently Functionalized Commodity Polymers as Tailor-Made Additives for Stereoselective Crystallization

Stereoselective inhibition of the nucleation and crystal growth of one enantiomer aided by “tailor-made” polymeric additives is an efficient method to obtain enantiopure compounds. However, the conventional preparation of polymeric additives from chiral monomers are laborious and limited in structures, which impedes their rapid optimization and applicability. Herein, we report a “plug-and-play” strategy to facilitate synthesis by using commercially available achiral polymers as the platform to attach various chiral small molecules as the recognition side-chains through non-covalent interactions. A library of supramolecular polymers made up of two vinyl polymers and six small molecules were applied with seeds in the selective crystallization of seven racemates in different solvents. They showed good to excellent stereoselectivity in yielding crystals with high enantiomeric purities in conglomerates and racemic compound forming systems. This convenient, low-cost modular synthesis strategy of polymeric additives will allow for high-efficient, economical resolution of various racemates on different scales.

Mechanism of eukaryotic serine racemase-catalyzed serine dehydration

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Colony-wise Analysis of a Theonella swinhoei Marine Sponge with a Yellow Interior Permitted the Isolation of Theonellamide i

There are several examples of marine organisms whose metabolic profiles differ among conspecifics inhabiting the same region. We have analyzed the metabolic profile of each colony of a Theonella swinhoei marine sponge with a yellow interior and noticed the patchy distribution of one metabolite. This compound was isolated and its structure was studied by a combination of spectrometric analyses and chemical degradation, showing it to be a congener in the theonellamide class of bicyclic peptides. Theonellamides had previously been isolated by us only from T. swinhoei with a white interior and not from those with a yellow interior.

Preparation and purification method of amino acid compound

The invention relates to the field of industrial organic synthesis, in particular to a preparation and purification method of an amino acid compound. The method comprises the following steps that (1)alpha-amino nitrile compounds or hydantoin compounds or mixtures thereof are heated to react to obtain alpha-amino acid salt under the condition that volatile alkali and a suitable solvent exist; (2)after the alpha-amino acid salt obtained in step (1) is distilled, the alpha-amino acid salt is recrystallized in an organic solvent to obtain the alpha-amino acid compound. According to the method, reaction conditions are mild, materials can be recycled, and introduction of metal ions and use of ammonium carbonate salt are avoided, so that post-treatment is simple and no waste salt is generated.

A α - amino acid compound synthesis and purification method

The invention relates to a synthesis and purification method for an alpha-amino acid compound. The synthesis and purification method is characterized by comprising the following steps: (1) adding substituted alpha-amino nitrile or a substituted hydantoin-based compound into alkali M(OH)x or metal oxide MxO, adding water or an alcohol and water mixed solvent, and heating for reaction to obtain alpha-amino acid salt; (2) adding ammonium carbonate or ammonium bicarbonate or introducing carbon dioxide into the solution in the step (1), separating to obtain filter liquor and precipitates MxHyCO3, performing reduced pressure concentration on the filter liquor, and recrystallizing in an alcohol solvent to obtain the alpha-amino acid compound (I). The synthesis and purification method for the alpha-amino acid compound is simple, the yield and purity of the obtained alpha-amino acid compound are high; furthermore, recycling utilization and cleaning production of materials can be realized; the synthesis and purification method is especially suitable for synthesis of the alpha-amino acid compound with high water solubility.

COMPOUND EXHIBITING REGULATORY ACTIVITY ON LYSOPHOSPHATIDYLSERINE RECEPTOR FUNCTION

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Stellettapeptins A and B, HIV-inhibitory cyclic depsipeptides from the marine sponge Stelletta sp.

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SEPARATING AGENT AND MANUFACTURING METHOD THEREOF

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