329013-12-9

Usage

Uses

BOC-(R)-3-Amino-3-(4-hydroxy-phenyl)-propionic acid is used as a chemical intermediate in the synthesis of various compounds for scientific research and pharmaceutical development. Its unique structure and functional groups make it a valuable component in the creation of new molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
BOC-(R)-3-Amino-3-(4-hydroxy-phenyl)-propionic acid is used as a building block for the development of new drugs, particularly in the synthesis of complex molecules with potential therapeutic applications. Its presence in the compound allows for the exploration of novel chemical pathways and interactions with biological targets, which could lead to the discovery of new treatments for various diseases.
Used in Research and Development:
BOC-(R)-3-Amino-3-(4-hydroxy-phenyl)-propionic acid is used as a research tool in the study of chemical reactions and mechanisms, as well as in the investigation of the properties and behavior of chiral compounds. Its unique structure and functional groups provide a platform for understanding the role of stereochemistry in chemical processes and the development of enantioselective synthetic methods.
Note: Due to the limited information provided, the specific applications of BOC-(R)-3-Amino-3-(4-hydroxy-phenyl)-propionic acid may require further research or consultation with chemical experts to fully understand its potential uses and benefits in various industries.

InChI:InChI=1/C14H19NO5/c1-14(2,3)20-13(19)15-11(8-12(17)18)9-4-6-10(16)7-5-9/h4-7,11,16H,8H2,1-3H3,(H,15,19)(H,17,18)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 73025-68-0 (R)-3-amino-3-(4-hydroxyphenyl)propanoic acid 
• 6049-54-3 3-amino-3-(4-hydroxyphenyl)propionic acid 
• 499995-80-1 C₁₄H₁₉NO₅ 
• 123-08-0 4-hydroxy-benzaldehyde 
• 329013-03-8 3-(4-hydroxy-phenyl)-3-phenylacetylamino-propionic acid 

Downstream Products

• 131791-82-7 methyl (-)-(3R)-3-amino-3-(4-methoxyphenyl)propanoate 
• 1218781-43-1 C₂₂H₃₄N₂O₆ 
• 1218781-47-5 C₃₃H₅₃N₅O₆ 
• 1218781-44-2 C₁₇H₂₆N₂O₄ 
• 73025-68-0 (R)-3-amino-3-(4-hydroxyphenyl)propanoic acid 

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.

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.