6310-42-5

Usage

Role in Citric Acid Cycle

Key molecule in the citric acid cycle, responsible for ATP production in mitochondria.

Metabolism

Important intermediate in the metabolism of carbohydrates, fats, and proteins.

Tricarboxylic Acid Cycle

Plays a critical role in the tricarboxylic acid cycle (also known as the Krebs cycle or TCA cycle).

Amino Acid Synthesis

Involved in the synthesis of amino acids, particularly glutamate and glutamine.

Neurotransmitter Production

Serves as a precursor for the production of the neurotransmitter GABA (gamma-aminobutyric acid).
Chronic fatigue syndrome
Alzheimer's disease
Cancer
Antioxidant properties
Anti-inflammatory properties

This molecule's properties and roles make it a significant component in cellular metabolism and potential therapeutic interventions.

Upstream product

• 34029-31-7 (S)-3-amino-3,4-dihydrofurane-2,5-dione hydrochloride 
• 71-43-2 benzene 
• 223581-87-1 (S)-ethyl 3-benzoyl-2-((trimethylsilyl)ethanesulfonylamino)propanoate 
• 651036-55-4 (3-hydroxy-1-(S)-hydroxymethyl-3-phenylpropyl)-carbamic acid tert-butyl ester 
• 104413-44-7 L-aspartic anhydride hydrochloride 
• 1379537-13-9 C₁₇H₂₅NO₄S 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 246040-05-1 2-tert-butoxycarbonylamino-4-oxo-4-phenyl-butyric acid 
• 172479-51-5 (2S)-2-tert-butoxycarbonylamino-4-oxo-4-phenylbutyric acid methyl ester 
• 396662-53-6 (S)-2-Benzoylamino-4-oxo-4-phenyl-butyric acid ethyl ester 
• 111717-08-9 t-butyl 2-(t-butoxycarbonylamino)-4-oxo-4-phenylbutanoate 

Downstream Products

• 384835-42-1 (1R,3R)-N-(3-hydroxy-1-hydroxymethyl-3-phenylprop-1-yl)dodecanamide 
• 399041-11-3 (2R)-2-dodecanoylamino-4-oxo-4-phenylbutyric acid ethyl ester hydrochloride 
• 383418-30-2 (1R,3S)-dodecanoic acid (3-hydroxy-1-hydroxymethyl-3-phenylpropyl)amide 

Relevant academic research and scientific papers

Synthesis of Unnatural α-Amino Acid Derivatives via Light-Mediated Radical Decarboxylative Processes

Unnatural amino acids (UAAs) are key building blocks with widespread application across several scientific fields. Therefore, it is highly attractive to develop straightforward and simple methodologies capable of granting quick access to these species. Herein we report a light-mediated protocol for the synthesis of UAA via radical decarboxylative processes. This methodology, which employs readily available and abundant starting materials – such as carboxylic and α-keto acids – proceeds under very mild reaction conditions and shows a high functional group tolerance. In addition, the products of the radical reaction can be readily derivatized to grant rapid access to complex UAAs. (Figure presented.).

Synthetic method of L-high phenylalanine

The invention relates to a synthetic method of L-high phenylalanine, and belongs to the technical field of compound synthesis. The synthetic method comprises the following steps: (1) dehydrating: making raw materials react with phosphorus trichloride to be made into L--aspartic anhydride hydrochloride; (2) carrying out acylation: taking sulfonated graphene as a catalyst, and performing a Friedel-Crafts reaction with benzene; (3) carrying out reduction: carrying out a hydrogenation reaction on carbonyl groups under the catalysis of palladium-carbon to obtain L-high phenylalanine hydrochloride; (4) performing neutralization: using alkaline water to neutralize hydrochloride, carrying out cooling crystallization and centrifugal filtration to obtain the product, namely L-high phenylalanine. The L-high phenylalanine disclosed by the invention is greatly reduced in catalyst amount, is 0.5 to 20% of the mass of a substrate, and further easy to separate and high in purity of an acylated product and further reduces influence on a subsequent carbonyl reduction reaction, the purity of the final product (HPLC) reaches up to more than 99.5%, and the overall yield can reach more than 90%, so that the L-high phenylalanine has good industrial production prospects.

A highly diastereoselective decarboxylative mannich reaction of β-keto acids with optically active N-sulfinyl α-imino esters

A range of protected γ-oxo-α-amino esters have been prepared in a highly regio- and stereoselective manner through the decarboxylative Mannich reaction of β-keto acids with optically active N-tert-butanesulfinyl α-imino esters in the presence of 3 mol % La(OTf)3 or 5 mol % Y(OTf)3 at 20 °C. Preliminary mechanistic studies indicate that the reaction proceeds through imine addition followed by decarboxylation.

Synthesis of novel chiral oxazoline ligands and application in the highly enantioselective diethylzinc addition to N-diphenylphosphinoylimines

Two sets of novel chiral oxazoline ligands were designed and conveniently prepared from readily available l-aspartic acid and evaluated in enantioselective diethylzinc addition to N-diphenylphosphinoyl imines. In the presence of stoichiometric amounts of these ligands, high enantioselectivities (up to 95% ee) and yields (up to 85%) were achieved for several aromatic imines in toluene at room temperature. Furthermore, the effect of the structure of the ligand on the reaction was studied.

Highly functionalised organolithium and organoboron reagents for the preparation of enantiomerically pure α-amino acids

Homochiral, highly functionalised organolithium reagents derived from l-serine have been generated and reacted with electrophiles. The novel enantiomerically pure adducts thus obtained were then converted, through β-amino alcohols, into novel non-proteinogenic α-amino acids. The methodology also made available a novel boronic acid which was then employed as a Suzuki cross-coupling partner, elaborating a new pathway to phenylalanine analogues.

Highly Functionalized Organolithium Reagents for Enantiomerically Pure α-Amino Acid Synthesis

(Equation presented) Highly functionalized L-serine-derived organolithium reagents have been generated and reacted with a variety of electrophiles, delivering novel enantiomerically pure adducts. These adducts were then converted into homochiral amino alcohols and novel nonproteinogenic α-amino acids, including an aspartic acid mimic that has been synthesized in an enantiomerically pure form for the first time.

Catalytic, enantioselective alkylation of α-imino esters: The synthesis of nonnatural α-amino acid derivatives

Methodology for the practical synthesis of nonnatural amino acids has been developed through the catalytic, asymmetric alkylation of α-imino esters and N1O-acetals by enol silanes, ketene acetals, alkenes, and allylsilanes using chiral transiti

Amino Acid Anhydride Hydrochlorides as Acylating Agents in Friedel-Crafts Reaction: A Practical Synthesis of L-Homophenylalanine

The use of amino acid hydrochlorides as acylating agents in Friedel-Crafts reaction is presented for the first time. A practical and convenient route to L-homophenylalanine from L-aspartic acid in 3 steps in 80 percent overall yield with >99 percent ee is thus achieved.

2-AMINO-4-PHENYL-4-OXO-BUTYRIC ACID DERIVATIVES

Use in the prevention and/or in the treatment of neurodegenerative diseases of 2-amino-4-phenyl-4-oxo-butyric acid derivatives which act as kynureninase enzyme inhibitors and/or kynurenine-3-hydroxylase enzyme inhibitors. Several of these derivatives are new and, as such, constitute a further object of this invention, together with the process for their preparation and the pharmaceutical compositions containing them.

Catalytic, enantioselective alkylations of N,O- and N,N-acetals and hemiacetals

We report the first examples of catalytic, enantioselective alkylation of N,O-acetals to produce useful amino acid derivatives 5 in high yield (73- 93%) and enantioselectivity (70-96%). We have extended the utility of our reaction to include a simple one-pot procedure from readily available starting materials. We also provide several different N-based protecting groups that greatly increase the flexibility of the reaction. In addition, we have elucidated novel mechanistic information including the discovery of unique transilylations that start off the catalytic reactions of enol silane nucleophiles with N,O-acetals. These details will guide us in further explorations of the reaction's scope and utility.