119817-54-8

Basic information

• Product Name: (S)-2-AMINO-4-OXO-4-PHENYLBUTANOIC ACID
• Synonyms: (S)-2-AMINO-4-OXO-4-PHENYLBUTANOIC ACID;3-BENZOYL-L-ALANINE
• CAS NO: 119817-54-8
• Molecular Formula: C₁₀H₁₁NO₃
• Molecular Weight: 193.2
• Mol File: 119817-54-8.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-2-AMINO-4-OXO-4-PHENYLBUTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-AMINO-4-OXO-4-PHENYLBUTANOIC ACID(119817-54-8)
• EPA Substance Registry System: (S)-2-AMINO-4-OXO-4-PHENYLBUTANOIC ACID(119817-54-8)

Safety Data

• Hazardous Substances Data: 119817-54-8(Hazardous Substances Data)

Usage

General Description

(S)-2-amino-4-oxo-4-phenylbutanoic acid, also known as L-phenylglycine, is a chemical compound with the molecular formula C10H11NO3. It is an alpha-amino acid and a non-proteinogenic amino acid, which means that it is not used in the synthesis of proteins. L-phenylglycine is used in the pharmaceutical industry as a building block for the synthesis of various pharmaceutical compounds, particularly for the production of antibiotics and other medications. It is also used in the production of certain flavors and fragrances. Additionally, L-phenylglycine has been studied for its potential role in the treatment of certain neurological and psychiatric disorders, although further research is needed to fully understand its effects and potential applications in these areas.

Upstream product

• 5817-92-5 2,4-dioxo-4-phenylbutanoic acid 
• 622-42-4 1-nitro-1-phenylmethane 
• 98-86-2 acetophenone 
• 119768-74-0 t-butyl 2-acetylamino-4-oxo-4-phenylbutanoate 
• 934-56-5 trimethyl(phenyl)stannane 
• 332072-75-0 (S)-(+)-N-[3,3-(ethylenedioxy)-3-phenylpropylidene]-p-toluenesulfinamide 
• 125261-01-0 2-(2-phenyl-1,3-dioxolan-2-yl)acetaldehyde 
• 27773-03-1 ethyl 3,3-(ethylenedioxy)-3-phenylpropanoate 
• 98-83-9 isopropenylbenzene 
• 216780-98-2 (2S)-4-phenyl-2-(toluene-4-sulfonylamino)-pent-4-enoic acid ethyl ester 
• 77130-15-5 2-phenylallyltrimethylsilane 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 332072-80-7 (S)-(+)-(N-(S)-p-toluenesulfinyl)-2-amino-3,3-(ethylenedioxy)-3-phenylpropanonitrile 
• 200730-99-0 (S)-2-trifluoroacetylamino-4-oxo-4-phenyl-butanoic acid 

Downstream Products

• 221122-90-3 (S)-2-benzyloxycarbonylamino-4-oxo-4-phenyl-butanoic acid 
• 246040-04-0 (S)-2-Allyloxycarbonylamino-4-oxo-4-phenyl-butyric acid 
• 246040-07-3 (S)-1-((S)-2-Benzyloxycarbonylamino-4-oxo-4-phenyl-butyryl)-pyrrolidine-2-carboxylic acid methyl ester 
• 246040-11-9 (3S,6S,8R,8aR)-6-Benzyloxycarbonylamino-8-hydroxy-5-oxo-8-phenyl-octahydro-indolizine-3-carboxylic acid methyl ester 
• 246040-09-5 (S)-1-((S)-2-tert-Butoxycarbonylamino-4-oxo-4-phenyl-butyryl)-pyrrolidine-2-carboxylic acid benzyl ester 
• 246040-13-1 (3S,6S,8R,8aR)-6-tert-Butoxycarbonylamino-8-hydroxy-5-oxo-8-phenyl-octahydro-indolizine-3-carboxylic acid benzyl ester 
• 221122-69-6 (S)-2-benzyloxycarbonylamino-4-oxo-4-phenyl-butanoyl azetidine 
• 221122-70-9 (S)-2-benzyloxycarbonylamino-4-oxo-4-phenyl-butanoyl pyrrolidine 
• 221122-71-0 (S)-2-benzyloxycarbonylamino-4-oxo-4-phenyl-butanoyl piperidine 
• 221122-72-1 (S)-2-benzyloxycarbonylamino-4-oxo-4-phenyl-butanoyl azepanine 

Relevant articles and documents

Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts

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Asymmetric synthesis of nonproteinogenic amino acids with l-amino acid transaminase: synthesis of (2S)-2-amino-4-oxo-4-phenylbutyric and (3E,2S)-2-amino-4-phenylbutenoic acids

2,4-Dioxo-4-phenylbutyric acid and 2-oxo-4-phenylbut-3-enoic acid are converted to the corresponding (S)-2-amino acids by recombinant Escherichia coli whole cells over-expressing aromatic transaminase from Enterobacter sp. BK2K-1 (AroATEs) in high yields (68-78%) and high enantiomeric purity (>99%) using l-aspartic acid as an amino donor.

Masked oxo sulfinimines (N-sulfinyl imines) in the asymmetric synthesis of proline and pipecolic acid derivatives.

[structure: see text]. On addition of Et2AlCN/i-PrOH, masked oxo sulfinimines give alpha-amino nitriles that afford oxo alpha-amino acids on hydrolysis. These amino acids cyclize and are reduced to cis proline and cis pipecolic acids derivatives in high ee and good yield. This new procedure avoids many of the limitations related to the preparation of oxo amino acids from proteinogenic amino acids.