102281-45-8

Basic information

• Product Name: D-4-AMINOPHENYLALANINE
• Synonyms: H-D-PHE(4-NH2)-OH;D-4-AMINOPHE;D-4-AMINOPHENYLALANINE;4-AMINO-D-PHENYLALANINE;P-AMINO-D-PHENYLALANINE;(R)-2-AMINO-3-(4-AMINOPHENYL)PROPANOIC ACID;(R)-2-AMINO-3-(4-AMINO PHENYL)-PROPIONIC ACID;4-AMINO-D-PHENYLALANINE HYDRATE, 98%
• CAS NO: 102281-45-8
• Molecular Formula: C₉H₁₂N₂O₂
• Molecular Weight: 180.2
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Chiral Compound;a-amino
• Mol File: 102281-45-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 268-270 °C(lit.)
• Boiling Point: 383.5 °C at 760 mmHg
• Flash Point: 185.8 °C
• Appearance: /white powder
• Density: 1.289 g/cm³
• Vapor Pressure: 1.44E-06mmHg at 25°C
• Refractive Index: 1.63
• Storage Temp.: 2-8°C
• Solubility: H2O: 20 mg/mL, soluble
• PKA: 2.14±0.10(Predicted)
• CAS DataBase Reference: D-4-AMINOPHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: D-4-AMINOPHENYLALANINE(102281-45-8)
• EPA Substance Registry System: D-4-AMINOPHENYLALANINE(102281-45-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 102281-45-8(Hazardous Substances Data)

Usage

General Description

D-4-aminophenylalanine is a chemical compound that is an enantiomer of the amino acid phenylalanine. It is commonly used as a building block in the synthesis of peptides and proteins, and it is crucial in medicinal chemistry for the production of pharmacological agents. D-4-aminophenylalanine is also being researched for its potential applications in the treatment of mood and cognitive disorders. Due to its role in biosynthesis and its potential therapeutic uses, D-4-aminophenylalanine is an important compound in pharmaceutical and biomedical research.

InChI:InChI=1/C9H12N2O2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,10-11H2,(H,12,13)/t8-/m1/s1

Upstream product

• 7647-01-0 hydrogenchloride 
• 103156-14-5 4-amino-N-benzoyl-D-phenylalanine-((1R)-menthyl ester) 
• 2922-41-0 (p-aminophenyl)alanine 
• 949-99-5 4-nitro-3-phenyl-L-alanine 

Downstream Products

• 297734-00-0 4-(bis-(2-hydroxyethyl)amino)-L-phenylalanine 
• 1188927-24-3 3-(4-(bis-(2-hydroxyethyl)amino)phenyl)-2-(2-hydroxyethylamino)-propanoic acid 
• 240428-60-8 N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-(4-methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-4-amino-3-chloro-D-phenylalanine 
• 240428-79-9 cyclo<2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-3-chloro-4-amino-D-phenylalanyl> 
• 240429-09-8 N-acetyl-4-(acetylamino)-3-chloro-D-phenylalanine 
• 240429-08-7 N-acetyl-4-(acetylamino)-D-phenylalanine methyl ester 
• 240428-46-0 4-amino-3-chloro-D-phenylalanine 
• 162178-70-3 1-[N²-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysyl]-4-(1,1-dimethylethoxycarbonyl)piperazine 
• 162175-92-0 1-[N²-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysyl]-4-(4-pyridinyl)piperazine 
• 162176-00-3 1-[N²-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysyl]-4-phenylpiperazine 
• 162176-16-1 N²-[4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine-2-phenethylamide 
• 162176-81-0 N²-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine-phenylamide 
• 162178-96-3 N²-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine 
• 864739-07-1 N²-[4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine methyl ester 

Relevant articles and documents

Deracemization and stereoinversion to aromatic d-amino acid derivatives with ancestral l-amino acid oxidase

Enantiomerically pure amino acid derivatives could be foundational compounds for peptide drugs. Deracemization of racemates to l-amino acid derivatives can be achieved through the reaction of evolved d-amino acid oxidase and chemical reductants, whereas deracemization to d-amino acid derivatives has not progressed due to the difficulty associated with the heterologous expression of l-amino acid oxidase (LAAO). In this study, we succeeded in developing an ancestral LAAO (AncLAAO) bearing broad substrate selectivity (13 l-amino acids) and high productivity through an Escherichia coli expression system (50.7 mg/L). AncLAAO can be applied to perform deracemization to d-amino acids in a similar way to deracemization to l-amino acids. In fact, full conversion (>99% ee, d-form) could be achieved for 16 racemates, including nine d,l-Phe derivatives, six d,l-Trp derivatives, and a d,l-phenylglycine. Taken together, we believe that AncLAAO could be a key enzyme to obtain optically pure d-amino acid derivatives in the future.

Process Of Making Optically Pure Melphalan

This invention provides a process of making 4-(bis-(2-hydroxyethyl)amino)-L-phenylalanine of the formula by hydroxyethylation, in a regioselective manner, of the aromatic amino group rather than the glycinic amino group.