203569-04-4

Basic information

• Product Name: BOC-DL-O-TYROSINE
• Synonyms: BOC-DL-O-TYROSINE;(R,S)-N-(tert-butoxycarbonyl)-o-tyrosine;Boc-2-hydroxy-DL-phenylalanine;N-Boc-DL-2-hydroxy-Phenylalanine
• CAS NO: 203569-04-4
• Molecular Formula: C₁₄H₁₉NO₅
• Molecular Weight: 281.3
• Mol File: 203569-04-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BOC-DL-O-TYROSINE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-DL-O-TYROSINE(203569-04-4)
• EPA Substance Registry System: BOC-DL-O-TYROSINE(203569-04-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 203569-04-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
BOC-DL-O-Tyrosine is utilized as a protecting group in peptide synthesis for the selective modification of other functional groups, ensuring the accurate formation of desired peptide sequences.
Used in Peptide Synthesis:
BOC-DL-O-Tyrosine is used as a building block in the synthesis of peptides, contributing to the development of new drug molecules and therapeutic agents.
Used in Medicinal Chemistry:
BOC-DL-O-Tyrosine plays a crucial role in medicinal chemistry, serving as a key component in the design and synthesis of novel pharmaceutical compounds with potential therapeutic applications.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 709-16-0 2-hydroxy-phenylalanine 

Relevant articles and documents

Design and synthesis of enantiomers of 3,5-dinitro-o-tyrosine: α- amino-3-hydroxy-5-methyl-4-isoxazolepropanoic acid (AMPA) receptor antagonists

The R- and S-isomers of 3,5-dinitro-o-tyrosine (6a,b) have been synthesized though the use of chemoenzymatic synthesis and shown to bind differentially with the α-amino-3-hydroxy-5-methyl-4-isoxazolepropanoic acid (AMPA, 3) receptors. The phenolic functional group of these o-tyrosine analogues was designed to act as a bioisostere of the γ-carboxyl group of glutamate. The S-isomer of 3,5-dinitro-o-tyrosine (6b) was 6.5 times more potent than the R-isomer (6a) in inhibiting [3H]AMPA binding with IC50 values of 13 ± 7 and 84 ± 26 μM, respectively. The phenolic group was important for binding affinity since the methoxy compound 7 was less potent than the phenolic compound 6 in inhibiting the binding of AMPA. The free amino group was also shown to be important since the N-acetyl analogue 15 and the N-t-BOC compounds 16 and 17 exhibited very low affinity for the AMPA receptors. AMPA receptor functional tests showed that the o-tyrosine analogues are antagonists and that S-isomer 6b (IC50 = 630 ± 140 μM) was more potent than the racemate 6 (IC50 = 730 ± 88 μM) while the R-isomer 6a was inactive up to 1 mM concentration, which is consistent with the S- isomer having higher binding affinity than the R-isomer.