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

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

Uses

Used in Pharmaceutical Industry:
D-4-aminophenylalanine is used as a building block for the synthesis of peptides and proteins, contributing to the development of new pharmacological agents. Its unique properties allow for the creation of novel compounds with specific therapeutic effects.
Used in Medicinal Chemistry:
D-4-aminophenylalanine is used as a key component in the production of medicinal compounds, enabling the design of drugs with targeted actions and improved efficacy.
Used in Research and Development:
D-4-aminophenylalanine is utilized in research for its potential applications in the treatment of mood and cognitive disorders, providing a foundation for the discovery of new therapeutic approaches.
Used in Biomedical Research:
D-4-aminophenylalanine is employed in biomedical research to explore its role in biosynthesis and its potential as a therapeutic agent, furthering our understanding of its mechanisms of action and applications in medicine.

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) 
• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 2922-41-0 (p-aminophenyl)alanine 

Downstream Products

• 89919-57-3 (R)-3-(4-hydroxyphenyl)lactic acid 
• 240429-07-6 4-amino-D-phenylalanine methyl ester dihydrochloride 
• 240428-57-3 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-D-phenylalanine 
• 864739-06-0 (R)-4-amino-3,5-dibromophenylalanine 
• 864738-92-1 4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanine 
• 878486-06-7 4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanine methyl ester 
• 162179-03-5 4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanine 
• 864738-93-2 N²-[4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-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 
• 162178-96-3 N²-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine 
• 162176-81-0 N²-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine-phenylamide 
• 162176-16-1 N²-[4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine-2-phenethylamide 
• 162176-00-3 1-[N²-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysyl]-4-phenylpiperazine 
• 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 

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.

Reconstruction of Hyper-Thermostable Ancestral L-Amino Acid Oxidase to Perform Deracemization to D-Amino Acids

L-amino acid oxidases (LAAOs) with broad substrate specificity can be used in the deracemization of D,L-amino acids (D,L-AAs) to their D-enantiomers. Hyper-thermostable LAAO (HTAncLAAO) was designed through a combination of manual sequence data mining and ancestral sequence reconstruction. Soluble expression of HTAncLAAO (>50 mg/L) can be achieved using an E. coli system. HTAncLAAO, which recognizes seven L-AAs as substrates, exhibits extremely high thermal stability and long-term stability; the t1/2 value was 95 °C and 99 % ee, D-enantiomer). These results suggest that HTAncLAAO is an excellent biocatalyst to perform this deracemization.

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.