499995-80-1

Usage

Uses

Used in Pharmaceutical Industry:
(S)-BOC-BETA-TYR-OH is used as a building block for peptide synthesis, allowing for the creation of peptides with specific sequences and properties. The protective BOC group ensures that the amine group remains intact during the synthesis process, enabling selective deprotection and further modifications to achieve the desired peptide structure.
Used in Biotechnology Industry:
In the biotechnology field, (S)-BOC-BETA-TYR-OH serves as a key component in the development of bioactive peptides. Its protective BOC group allows for precise control over the synthesis process, resulting in peptides with targeted biological functions and applications, such as therapeutic agents or diagnostic tools.

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 
• 6049-54-3 3-amino-3-(4-hydroxyphenyl)propionic acid 
• 329013-03-8 3-(4-hydroxy-phenyl)-3-phenylacetylamino-propionic acid 
• 73025-68-0 (R)-3-amino-3-(4-hydroxyphenyl)propanoic acid 
• 2627-86-3 (S)-1-phenyl-ethylamine 

Downstream Products

• 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.