73025-68-0

Usage

Uses

Used in Pharmaceutical Industry:
(R)-4-HYDROXY-BETA-PHENYLALANINE is used as an active pharmaceutical ingredient for its potential therapeutic effects in the management of chronic pain and depression. Its role in neurotransmitter synthesis contributes to mood regulation and cognitive function, making it a valuable component in the development of medications targeting these conditions.
Used in Nutritional Supplements:
(R)-4-HYDROXY-BETA-PHENYLALANINE is used as a key ingredient in nutritional supplements designed to support overall well-being and mental health. Its involvement in neurotransmitter production helps to enhance mood, energy levels, and focus, making it a popular choice for individuals seeking to improve their cognitive and emotional health.
Used in Research and Development:
(R)-4-HYDROXY-BETA-PHENYLALANINE is utilized as a research compound in the development of new therapies and treatments for various neurological and psychological conditions. Its role in neurotransmitter synthesis and potential therapeutic effects make it an important subject of study for scientists and researchers in the fields of neuroscience and mental health.

Upstream product

• 329013-03-8 3-(4-hydroxy-phenyl)-3-phenylacetylamino-propionic acid 
• 166023-23-0 (R)-3-amino-3-(4-hydroxyphenyl)propionic acid tert-butyl ester 
• 691905-29-0 tert-butyl (E)-3-(4-benzyloxyphenyl)propenoate 
• 951174-28-0 tert-butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-3-(4-benzyloxyphenyl)propanoate 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 6049-54-3 3-amino-3-(4-hydroxyphenyl)propionic acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 499995-80-1 C₁₄H₁₉NO₅ 
• 329013-12-9 (S)-N-tert-butyloxycarbonyl β-Tyr 

Downstream Products

• 1448510-86-8 4'-O,3-N-((2S)-methylbutyryl)ethyl ester 
• 177966-66-4 (R)-β-tyrosine methyl ester 
• 329013-12-9 (S)-N-tert-butyloxycarbonyl β-Tyr 

Relevant academic research and scientific papers

Resolution synthesis method of 3-amino-3-(4-hydroxyphenyl)propionic acid

The invention relates to a resolution synthesis method of 3-amino-3-(4-hydroxyphenyl)propionic acid, mainly aiming at solving the technical problems of an existing synthesis method of more steps and high cost. The resolution synthesis method comprises the following steps: enabling p-hydroxybenzaldehyde to react with ammonium acetate and malonic acid in an ethanol solution to generate a compound 1; enabling the compound 1 to react with triethylamine and di-tert-butyl dicarbonate in a mixed solution of water and acetone to generate a compound 2; enabling the compound 2 to react with R(+)-1-phenethylamine in a tetrahydrofuran solution; acidifying an intermediate product with hydrochloric acid to generate a compound 3; enabling the compound 3 to react with an ethanol solution of hydrochloric acid to obtain hydrochloride, and enabling the hydrochloride to react with a sodium hydroxide water solution to obtain a target compound 4; enabling the compound 2 to react with S-1-phenethylamine in the tetrahydrofuran solution, and acidifying an intermediate product with the hydrochloric acid to generate a compound 5; enabling the compound 5 to react with the ethanol solution of the hydrochloric acid to obtain hydrochloride and enabling the hydrochloride to react with a sodium hydroxide water solution to obtain a target compound 6. (R)- and (S)-3-amino-3-(4-hydroxyphenyl)propionic acid is widely applied in a polypeptide biopharmaceutical industry.

Parallel synthesis of homochiral β-amino acids

The parallel asymmetric synthesis of an array of 30 β-amino acids of high enantiomeric purity using the conjugate addition of homochiral lithium N-benzyl-N-(α-methylbenzyl)amide as the key step is accomplished. The experimental simplicity and highly practical nature of the protocol is demonstrated by the efficient parallel conversion of 15 α,β-unsaturated esters to both enantiomeric series of the corresponding β-amino acids in high overall yields and selectivities with minimal purification involved in each step of the reaction protocol.

Homochiral lithium amides for the asymmetric synthesis of β-amino acids

Secondary homochiral lithium amides derived from α-methylbenzylamine undergo highly diastereoselective conjugate additions to a range of α,β-unsaturated esters. The corresponding β-amino acids are readily liberated by successive N-debenzylation and ester hydrolysis, furnishing (R)-β-amino butyric acid, (R)-β-amino pentanoic acid, (S)-β-leucine, (R)-β-amino octanoic acid, (S)-β-phenylalanine, (S)-β-tyrosine methyl ether, (S)-β-tyrosine hydrochloride and (S)-β-(2-methoxyphenyl)-β-amino propanoic acid in high yields and high ee. The application of this procedure to the synthesis of the natural products (R)-β-DOPA and (R)-β-lysine is demonstrated. The development of a simplified one-pot reaction protocol applicable to the multi-gram scale synthesis of homochiral β-amino esters is also delineated.

Synthesis and binding activity of endomorphin-1 analogues β-amino acids

Endomorphin-1 (Tyr-Pro-Trp-PheNH2) has been proposed as the most potent endogenous ligand of the μ-opioid receptors. In this paper, we describe the synthesis of some endomorphin-1 based tetrapeptides in which a residue of the sequence Tyr-Pro-Trp-PheNH2 is replaced by the corresponding β-isomer. These novel peptides showed different affinities for the opioid receptors labeled with [3H]-DAMGO in rat brain membranes, depending on the β-amino acid. In particular, the tetrapeptide containing β-Pro (Tyr-β-(R)-Pro-Trp-PheNH2) displayed a higher affinity than endogenous endomorphin-1, as revealed by their K(i) values (0.33 and 11.1 nM, respectively). (C) 2000 Elsevier Science Ltd.