33173-53-4

Usage

Uses

Used in Pharmaceutical Industry:
H-P-AZIDO-PHE-OH is used as a therapeutic agent for treating patients with depression. Its unique properties enable it to be incorporated into the treatment regimen, potentially offering new avenues for managing this condition.
Used in Biochemistry and Molecular Biology:
H-P-AZIDO-PHE-OH is used as a functionalization agent for protein modification. The azide group in the compound allows for the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) or copper-free strained internal alkyne (SPAAC) reactions, enabling the attachment of various molecules to proteins. This technique has been utilized for protein PEGylation, masking with sugars, and the attachment to antibodies, among other applications.
Used in Chemical Synthesis:
H-P-AZIDO-PHE-OH is used as a building block in the synthesis of various chemical compounds, particularly those requiring the unique reactivity of the azido group. Its nonpolar nature and essential amino acid origin make it a versatile component in the development of new molecules with specific functions and properties.

InChI:InChI=1/C9H10N4O2/c10-8(9(14)15)5-6-1-3-7(4-2-6)12-13-11/h1-4,8H,5,10H2,(H,14,15)

Upstream product

• 33173-55-6 (S)-3-(4-azidophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid 
• 103882-09-3 N-Boc-4-I-Phe-OH 
• 1991-81-7 4-iodo-L-phenylalanine 
• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 943-80-6 4-amino-L-phenylalanine 
• 63-91-2 L-phenylalanine 

Relevant academic research and scientific papers

Synthesis and Explosion Hazards of 4-Azido- l -phenylalanine

A reliable, scalable, cost-effective, and chromatography-free synthesis of 4-azido-l-phenylalanine beginning from l-phenylalanine is described. Investigations into the safety of the synthesis reveal that the Ullman-like Cu(I)-catalyzed azidation step does not represent a significant risk. The isolated 4-azido-l-phenylalanine product, however, exhibits previously undocumented explosive characteristics.

Distinct metabolites for photoreactive l-phenylalanine derivatives in Klebsiella sp. CK6 isolated from rhizosphere of a wild dipterocarp sapling

Photoaffinity labeling is a reliable analytical method for biological functional analysis. Three major photophores-aryl azide, benzophenone and trifluoromethyldiazirine- are utilized in analysis. Photophore-bearing L-phenylalanine derivatives, which are used for biological functional analysis, were inoculated into a Klebsiella sp. isolated from the rhizosphere of a wild dipterocarp sapling in Central Kalimantan, Indonesia, under nitrogen-limiting conditions. The proportions of metabolites were quite distinct for each photophore. These results indicated that photophores affected substrate recognition in rhizobacterial metabolic pathways, and differential photoaffinity labeling could be achieved using different photophore-containing L-phenylalanine derivatives.