65451-19-6

Basic information

• Product Name: (DL)-N-(Phenylacetyl)-3-amino-3-phenylpropanoic acid
• Synonyms: (DL)-N-(Phenylacetyl)-3-amino-3-phenylpropanoic acid;3-phenyl-3-(2-phenylacetamido)propanoic acid
• CAS NO: 65451-19-6
• Molecular Formula: C₁₇H₁₇NO₃
• Molecular Weight: 283.32
• Mol File: 65451-19-6.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (DL)-N-(Phenylacetyl)-3-amino-3-phenylpropanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (DL)-N-(Phenylacetyl)-3-amino-3-phenylpropanoic acid(65451-19-6)
• EPA Substance Registry System: (DL)-N-(Phenylacetyl)-3-amino-3-phenylpropanoic acid(65451-19-6)

Safety Data

• Hazardous Substances Data: 65451-19-6(Hazardous Substances Data)

Usage

Description

(DL)-N-(Phenylacetyl)-3-amino-3-phenylpropanoic acid is an organic compound derived from the amino acid phenylalanine, belonging to the family of alpha amino acids. It features a phenylacetyl functional group and a 3-amino-3-phenylpropanoic acid backbone, which contribute to its potential applications in various fields.

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

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

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 
• 263247-50-3 (R)-3-benzamido-3-phenylpropanoic acid 
• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 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 
• 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 articles and documents

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.

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.

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.