Production Method 1

1239710-15-6

943-73-7

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  rt; 20 h, reflux

Reference

Asymmetric synthesis of allylic secondary alcohols: a new general approach for the preparation of α-amino acids

Drummond, Lorna J.; Sutherland, Andrew, Tetrahedron, 2010, 66(29), 5349-5356

Production Method 2

63393-59-9

943-73-7

Reaction Conditions

1.1 Reagents: Cobalt chloride (CoCl2) Catalysts: Aminoacylase ,  Amino acid amide racemase Solvents: Water ;  1 h, pH 8, 37 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2

Reference

Enantioselective Synthesis of L-Homophenylalanine by Whole Cells of Recombinant Escherichia coli Expressing L-Aminoacylase and N-Acylamino Acid Racemase Genes from Deinococcus radiodurans BCRC12827

Hsu, Shih-Kuang; Lo, Hsueh-Hsia; Kao, Chao-Hung; Lee, Dong-Sheng; Hsu, Wen-Hwei, Biotechnology Progress, 2006, 22(6), 1578-1584

Production Method 3

168154-76-5

943-73-7

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium

Reference

Amino acid anhydride hydrochlorides as acylating agents in friedel-crafts reaction: A practical synthesis of L-homophenylalanine

Lin, Wenqing; He, Ze; Zhang, Haile; Zhang, Xiaomei; Mi, Aiqiao; et al, Synthesis, 2001, (7), 1007-1009

Production Method 4

710-11-2

943-73-7

Reaction Conditions

1.1 Reagents: NAD ,  Ammonium formate ,  Potassium hydroxide ,  Phosphoric acid Catalysts: Dehydrogenase ,  Formate dehydrogenase (NADP) Solvents: Water ;  15 - 20 h, pH 8, rt

Reference

Method for preparing L-homophenylalanine from 2-oxo-4-phenylbutyric acid or its ester with homophenylalanine dehydrogenase

, China, , ,

Production Method 5

168154-76-5

943-73-7

Reaction Conditions

1.1 Reagents: Hydrogen ,  Hydrochloric acid Catalysts: Palladium Solvents: Water ;  48 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  pH 7

Reference

Improved method of preparing 2(S)-amino-4-phenylbutyric acid

, World Intellectual Property Organization, , ,

Production Method 6

710-11-2

943-73-7

Reaction Conditions

1.1 Catalysts: Phenylalanine dehydrogenase

Reference

Enzymic manufacture of L-2-amino-4-phenylbutyric acid

, Japan, , ,

Production Method 7

139040-47-4

943-73-7

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium

Reference

Hydrogen

Wilt, Jeremy C.; Collier, Steven J., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2016, 1, 1-18

Production Method 8

56-84-8

943-73-7

Reaction Conditions

1.1 Reagents: Phosphorus trichloride Solvents: Acetic acid ,  Acetic anhydride ;  rt; 20 h, 40 °C
1.2 Catalysts: Graphene Solvents: Benzene ;  20 h, 180 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  -5 °C
1.4 Reagents: Hydrochloric acid ,  Oxygen Catalysts: Palladium Solvents: Water ;  0.2 MPa, 90 °C
1.5 Reagents: Ammonia ;  pH 5.5 - 5.8, 10 - 25 °C

Reference

Process for preparation of L-homophenylalanine

, China, , ,

Production Method 9

120379-81-9

943-73-7

Reaction Conditions

1.1 Reagents: Sodium carbonate Catalysts: Manganese dichloride ,  Hydrolase ,  Dihydropyrimidinase Solvents: Water ;  pH 7 - 7.5, 37 - 40 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 7 - 7.2; pH 5.5

Reference

Preparation method of L-phenylalanine or D-phenylalanine

, China, , ,

Production Method 10

1678511-73-3

943-73-7

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Methanol ;  7 h, 45 °C

Reference

Process for preparation of 4-phenyl-α-aminobutyric acid

, China, , ,

Production Method 11

710-11-2

943-73-7

Reaction Conditions

Reference

Industrial production of L-2-amino-4-phenylbutyric acid from 2-oxo-4-phenylbutyric acid by Paracoccus denitrificans containing aminotransferase activity

Senuma, Masaru; Nakamichi, Katsuhiko; Nabe, Koichi; Nishimoto, Shigeru; Tosa, Tetsuya, Applied Biochemistry and Biotechnology, 1989, 22(2), 141-50

Production Method 12

85808-34-0

943-73-7

Reaction Conditions

1.1 Reagents: Pyridoxal 5′-phosphate Catalysts: Cobalt chloride (CoCl2) ,  2-Aminohexano-6-lactam racemase ,  L-Amino acid amidase Solvents: Water ;  12 h, pH 7, 40 °C

Reference

Enzymatic Synthesis of Chiral Phenylalanine Derivatives by a Dynamic Kinetic Resolution of Corresponding Amide and Nitrile Substrates with a Multi-Enzyme System

Yasukawa, Kazuyuki; Asano, Yasuhisa, Advanced Synthesis & Catalysis, 2012, 354(17), 3327-3332

Production Method 13

2923083-64-9

943-73-7

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  3 h, rt

Reference

Preparation method of 2-(S)-amino-4-arylbutyric acid compound from 2-(S)-amino-4-oxo-4-arylbutyric acid by reduction, ring-closing esterification and hydrogenation

, China, , ,

Production Method 14

105382-09-0

943-73-7

Reaction Conditions

1.1 Reagents: Sodium carbonate Solvents: Methanol ;  5 min, rt

Reference

N-Acyliminium cyclization as an approach for an asymmetric synthesis of the pyrrolo[2,1-a]benzazepine ring system

Allin, Steven M.; Towler, Joannah M. R.; Elsegood, Mark R. J.; Saha, Basu; Page, Philip C. Bulman, Synthetic Communications, 2012, 42(6), 872-882

Production Method 15

710-11-2

56-87-1

943-73-7

Reaction Conditions

1.1 Catalysts: Pyridoxal 5′-phosphate ,  Aspartate aminotransferase Solvents: Water ;  24 h, pH 9.0, 37 °C; 37 °C → 100 °C

Reference

Asymmetrical Synthesis of L-Homophenylalanine Using Engineered Escherichia coli Aspartate Aminotransferase

Lo, Hsueh-Hsia; Hsu, Shih-Kuang; Lin, Wei-De; Chan, Nei-Li; Hsu, Wen-Hwei, Biotechnology Progress, 2005, 21(2), 411-415

Production Method 16

253327-94-5

943-73-7

Reaction Conditions

1.1 Reagents: Hydrochloric acid
1.2 Reagents: Sodium acetate

Reference

DPAMPP in catalytic asymmetric reactions: enantioselective synthesis of L-homophenylalanine

Xie, Yinong; Lou, Rongliang; Li, Zhi; Mi, Aiqiao; Jiang, Yaozhong, Tetrahedron: Asymmetry, 2000, 11(7), 1487-1494

Production Method 17

2379874-06-1

943-73-7

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Ethanol ,  Water ;  rt → 65 °C; 12 h, 1 bar, 65 °C

Reference

Nitroalkanes as Versatile Nucleophiles for Enzymatic Synthesis of Noncanonical Amino Acids

Romney, David K. ; Sarai, Nicholas S. ; Arnold, Frances H., ACS Catalysis, 2019, 9(9), 8726-8730

Production Method 18

100516-57-2

943-73-7

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium chloride Solvents: Ethanol ,  Tetrahydrofuran

Reference

Practical asymmetric syntheses of α-amino acids through carbon-carbon bond constructions on electrophilic glycine templates

Williams, Robert M.; Sinclair, Peter J.; Zhai, Dongguan; Chen, Daimo, Journal of the American Chemical Society, 1988, 110(5), 1547-57

Production Method 19

1012-05-1

943-73-7

Reaction Conditions

1.1 Reagents: Ammonium formate ,  Ammonia Solvents: Water ;  pH 7.2
1.2 Reagents: Oxygen Catalysts: Palladium ,  D-Amino acid oxidase ,  Catalase ;  24 h, 30 °C

Reference

Biocatalytic deracemization method for preparing non-natural L-amino acid using immobilized D-amino acid oxidase

, China, , ,

Production Method 20

104165-94-8

943-73-7

Reaction Conditions

1.1 Reagents: Magnesium stearate ,  Ethyl acrylate-methyl methacrylate-trimethylaminoethyl methacrylate chloride cop… Solvents: Acetone ;  25 °C; 3 h, 25 °C
1.2 Reagents: NAD ,  Ammonium formate ,  Sodium chloride Catalysts: Formate dehydrogenase ,  Phenylalanine dehydrogenase Solvents: Water ;  12 h, pH 8.0, 25 °C
1.3 Reagents: Sodium hydroxide Solvents: Water ;  pH 14, 25 °C

Reference

Microparticle-Based Strategy for Controlled Release of Substrate for the Biocatalytic Preparation of L-Homophenylalanine

Zhang, Jielin; Tao, Shanshan; Zhang, Baojie; Wu, Xuri; Chen, Yijun, ACS Catalysis, 2014, 4(5), 1584-1587

Production Method 21

46460-24-6

943-73-7

90940-54-8

Reaction Conditions

1.1 Catalysts: Triacylglycerol lipase Solvents: Water

Reference

Kinetic resolution of amino acid esters catalyzed by lipases

Houng, Jer-Yiing; Wu, May-Ling; Chen, Shui-Tein, Chirality, 1996, 8(6), 418-422

L-Homophenylalanine Raw materials

• 2-Oxo-4-phenylbutanoic Acid
• 2-amino-4-phenyl-butanoic acid
• L-Homophenylalanine hydrochloride
• Acetyl-d-homophenylalanine
• Benzenebutanoic acid, α-[(2,2,2-trichloroacetyl)amino]-, methyl ester, (αS)-
• 2-Amino-4-phenylbutanamide
• Benzenebutanoic acid, α-(acetylamino)-, ethyl ester, (αS)-
• Benzenebutanoic acid, α-azido-, (αS)-
• (S)-4-Oxo-homophenylalanine Hydrochloride
• (αS)-α-Amino-γ-nitrobenzenebutanoic acid
• L-Aspartic acid
• L-Lysine
• 4-Morpholinecarboxylic acid, 2-oxo-3-(2-oxo-2-phenylethyl)-5,6-diphenyl-, phenylmethyl ester, (3S,5S,6R)-
• 5-(2-phenylethyl)imidazolidine-2,4-dione
• ethyl 2-amino-4-phenylbutanoate
• 2(3H)-Furanone, 3-aminodihydro-5-phenyl-, (3S)-
• (αS)-α-[[(1S)-2-Hydroxy-1-phenylethyl]amino]benzenebutanoic acid
• sodium 2-oxo-4-phenylbutanoate

L-Homophenylalanine Preparation Products

• (R)-Ethyl 2-amino-4-phenylbutanoate hydrochloride (90940-54-8)
• L-Homophenylalanine (943-73-7)

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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives L-alpha-amino acids
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Introduction to L-Homophenylalanine (CAS No. 943-73-7)

L-Homophenylalanine, a derivative of the essential amino acid phenylalanine, is a compound of significant interest in the field of pharmaceutical chemistry and biochemistry. The molecular structure of this compound, characterized by its CAS number 943-73-7, includes a phenyl ring attached to an alpha-amino group and a carboxylic acid group. This unique configuration imparts distinct chemical and biological properties, making it a valuable subject of study and application in various scientific domains.

The synthesis and characterization of L-Homophenylalanine have been extensively explored in recent years, particularly in the context of its potential therapeutic applications. Researchers have been keenly interested in understanding how modifications to the phenylalanine backbone can influence its metabolic pathways and biological interactions. This has led to a growing body of literature on the compound's role in enzyme inhibition, neurotransmitter modulation, and as a precursor in the synthesis of more complex biomolecules.

One of the most compelling areas of research involving L-Homophenylalanine is its application in neurology. Studies have suggested that this compound may have neuroprotective properties, making it a candidate for treating neurodegenerative diseases such as Parkinson's and Alzheimer's. The phenyl ring in L-Homophenylalanine can interact with specific receptors and enzymes in the brain, potentially mitigating the oxidative stress and inflammation associated with these conditions. Recent preclinical trials have shown promising results, indicating that L-Homophenylalanine could be a viable therapeutic agent when combined with other treatments.

In addition to its neuroprotective potential, L-Homophenylalanine has also been investigated for its role in metabolic disorders. The compound's ability to modulate amino acid metabolism may help in managing conditions like phenylketonuria (PKU), where the body cannot properly metabolize phenylalanine. By serving as a substrate or analog, L-Homophenylalanine could help maintain balanced amino acid levels, thereby preventing the toxic accumulation of phenylalanine derivatives.

The chemical properties of L-Homophenylalanine make it an interesting candidate for drug design and development. Its structural similarity to natural amino acids allows it to be incorporated into peptide chains without significant disruption to biological pathways. This characteristic is particularly useful in creating enzyme inhibitors or modulators that target specific amino acid residues. Furthermore, the compound's stability under various physiological conditions enhances its suitability for pharmaceutical formulations.

Recent advancements in computational chemistry have also contributed to our understanding of L-Homophenylalanine's interactions within biological systems. Molecular dynamics simulations and quantum mechanical calculations have provided insights into how this compound binds to target proteins and enzymes. These computational studies are complemented by experimental approaches, such as X-ray crystallography and nuclear magnetic resonance (NMR) spectroscopy, which further elucidate the structural basis of its biological activity.

The industrial production of L-Homophenylalanine has also seen significant improvements, driven by demand from both academic research institutions and pharmaceutical companies. Modern biotechnological methods, including enzymatic synthesis and fermentation processes, have made it possible to produce high-purity L-Homophenylalanine on an industrial scale. These advancements ensure that researchers have access to sufficient quantities of the compound for their studies, thereby accelerating the pace of discovery.

The future prospects for L-Homophenylalanine are promising, with ongoing research exploring new therapeutic applications and refining existing ones. The compound's versatility as a building block for more complex molecules makes it an attractive candidate for drug development across multiple therapeutic areas. As our understanding of its biological mechanisms continues to grow, so too will its potential applications in medicine and biotechnology.

• 1012-05-1(2-amino-4-phenyl-butanoic acid)
• 56-45-1(L-Serine)
• 74-79-3(L-Arginine)
• 943-80-6(p-Amino-L-phenylalanine)
• 949-99-5((2S)-2-amino-3-(4-nitrophenyl)propanoic acid)
• 63-91-2(L-Phenylalanine)
• 63-68-3(L-Methionine)
• 1676-73-9(L-Glutamate-γ-benzyl ester)
• 673-06-3(D-Phenylalanine)
• 150-30-1(DL-3-Phenylalanine)