65451-19-6

Usage

Uses

Used in Biochemical Research:
(DL)-N-(Phenylacetyl)-3-amino-3-phenylpropanoic acid is used as a research compound for studying its properties and potential applications in the field of biochemistry.
Used in Drug Synthesis:
As a derivative of phenylalanine, (DL)-N-(Phenylacetyl)-3-amino-3-phenylpropanoic acid is utilized as a building block or intermediate in the synthesis of various pharmaceutical compounds.
Used in Pharmaceutical Development:
(DL)-N-(Phenylacetyl)-3-amino-3-phenylpropanoic acid is investigated for its potential therapeutic use in the treatment of neurological disorders and chronic pain due to its unique structure and functional groups.
Used in Laboratory Settings:
In the laboratory, (DL)-N-(Phenylacetyl)-3-amino-3-phenylpropanoic acid is employed as a tool for studying protein synthesis and structure, contributing to a better understanding of these biological processes.
Used in the Pharmaceutical Industry:
(DL)-N-(Phenylacetyl)-3-amino-3-phenylpropanoic acid is used as an active pharmaceutical ingredient (API) for the development of new drugs targeting neurological conditions and pain management.
Used in the Biotechnology Industry:
(DL)-N-(Phenylacetyl)-3-amino-3-phenylpropanoic acid is used as a key component in the design and development of novel biotechnological applications, potentially including enzyme catalysis and protein engineering.

Upstream product

• 100-52-7 benzaldehyde 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 103-80-0 phenylacetyl chloride 

Downstream Products

• 83649-48-3 (R)-3-amino-3-phenylpropionic acid hydrochloride 
• 65414-83-7 (S)-3-phenyl-3-(2-phenylacetamido)propanoic acid 
• 161024-80-2 (R)-3-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid 
• 1010816-39-3 (R)-3-phenyl-3-(2-phenylacetamido)propanoic acid 
• 614-19-7 (R)-3-phenyl-3-aminopropionic acid 
• 614-19-7 (S)-3-amino-3-phenylpropanoic acid 
• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 263247-50-3 (R)-3-benzamido-3-phenylpropanoic acid 
• 146848-91-1 (4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester 
• 144494-74-6 (R)-3-benzamido-3-phenylpropanoic acid methyl ester 

Relevant academic research and scientific papers

Enantioselective acylation of β-phenylalanine acid and its derivatives catalyzed by penicillin G acylase from alcaligenes faecalis

This study developed a simple, efficient method for producing racemic β-phenylalanine acid (BPA) and its derivatives via the enantioselective acylation catalyzed by the penicillin G acylase from Alcaligenes faecalis (Af-PGA). When the reaction was run at 25°C and pH 10 in an aqueous medium containing phenylacetamide and BPA in a molar ratio of 2:1, 8 U/mL enzyme and 0.1 M BPA, the maximum BPA conversion efficiency at 40 min only reached 36.1%, which, however, increased to 42.9% as the pH value and the molar ratio of phenylacetamide to BPA were elevated to 11 and 3:1, respectively. Under the relatively optimum reaction conditions, the maximum conversion efficiencies of BPA derivatives all reached about 50% in a relatively short reaction time (45-90 min). The enantiomeric excess value of product (eep) and enantiomeric excess value of substrate (ees) were all above 98% and 95%, respectively. These results suggest that the method established in this study is practical, effective, and environmentally benign and may be applied to industrial production of enantiomerically pure BPA and its derivatives.

Development of a commercial process for (S)-β-phenylalanine (1)

The development of a commercial manufacturing route for (S)-β-phenylalanine 8, a key pharmaceutical building block, is described. The different approaches which were investigated, based on catalytic asymmetric hydrogenation of enamide intermediates and on biocatalysis using acylase and lipase hydrolyses, are compared. The lipase resolution route was chosen for scale-up, and the final two-step process, based on readily available raw materials, is shown to be robust at full manufacturing scale

An expedient synthesis of 6-arylpiperidine-2,4-diones by chain-extension of β-aryl-β-aminoacids

The synthesis of novel 6-arylpiperidine-2,4-diones is described in five steps starting from β-aryl-β-aminoacids via the chain extension of the latter into δ-aryl-δ-amino-β-ketoacids. The chemical pathway involves an acylation of Meldrum's acid and yields useful building blocks for heterocyclic chemistry.

Synthesis and binding activity of endomorphin-1 analogues β-amino acids

Endomorphin-1 (Tyr-Pro-Trp-PheNH2) has been proposed as the most potent endogenous ligand of the μ-opioid receptors. In this paper, we describe the synthesis of some endomorphin-1 based tetrapeptides in which a residue of the sequence Tyr-Pro-Trp-PheNH2 is replaced by the corresponding β-isomer. These novel peptides showed different affinities for the opioid receptors labeled with [3H]-DAMGO in rat brain membranes, depending on the β-amino acid. In particular, the tetrapeptide containing β-Pro (Tyr-β-(R)-Pro-Trp-PheNH2) displayed a higher affinity than endogenous endomorphin-1, as revealed by their K(i) values (0.33 and 11.1 nM, respectively). (C) 2000 Elsevier Science Ltd.

A new diastereoselective synthesis of anti-α-alkyl α-hydroxy β-amino acids

As part of an ongoing project concerning the synthesis of enantiomerically pure α-hydroxy β-amino acids, we have now developed a general strategy allowing the synthesis of anti-α-alkyl α-hydroxy β-amino acids. Our procedure involves the intermediate formation of trans-oxazolines, which are alkylated at C-5 with good to high diastereoselectivity and then hydrolysed under mildly acidic conditions, affording in quantitative yield the corresponding hydroxy amides. The starting (R)-3-amino-3-phenylpropanoic acid and (S)-3-aminobutanoic acid were obtained in enantiomerically pure form by selective enzymatic hydrolysis of the corresponding phenylacetylamides with penicillin G acylase.

Biocatalytic approach to enatiomerically pure β-amino acids

β-Aryl-β-amino acids were prepared in good chemical yield and high enantiomeric purity (> 95% ee) via penicillin acylase-catalyzed hydrolysis of the corresponding N-phenylacetyl derivatives. The (R)-enantiomers were the fast-reacting isomers in all cases studied. The biocatalytic procedure described employs a very simple set of reactions using inexpensive commercially available chemicals and enzyme, and could be easily scaled up.