4-Azido-L-phenylalanine

Base Information

• Chemical Name: 4-Azido-L-phenylalanine
• CAS No.: 33173-53-4
• Molecular Formula: C₉H₁₀N₄O₂
• Molecular Weight: 206.204
• Hs Code.: 2929909090
• European Community (EC) Number: 810-082-7
• DSSTox Substance ID: DTXSID10186829
• Nikkaji Number: J1.653.931G
• Wikidata: Q76279767
• Mol file: 33173-53-4.mol

Synonyms:4-azido-L-phenylalanine;4-azidophenylalanine;4-azidophenylalanine, monohydrochloride;azidophenylalanine;p-azidophenylalanine

Chemical Property of 4-Azido-L-phenylalanine

Chemical Property:

• PSA: 113.07000
• LogP: 1.73586
• Storage Temp.: -15°C
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 206.08037557
• Heavy Atom Count: 15
• Complexity: 267

Purity/Quality:

97% ^*data from raw suppliers

4-Azido-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(C(=O)O)N)N=[N+]=[N-]
• Isomeric SMILES: C1=CC(=CC=C1C[C@@H](C(=O)O)N)N=[N+]=[N-]
• General Description: H-P-AZIDO-PHE-OH, also known as p-azidophenylalanine, is a clickable unnatural amino acid (UAA) that has been explored for single-molecule fluorescence resonance energy transfer (smFRET) studies. While the study highlights the advantages of propargyllysine (UAA 5) for high-resolution smFRET due to its superior probe accessibility, expression yield, and labeling efficiency, p-azidophenylalanine remains a viable option for bioorthogonal labeling strategies. Its azide group enables selective conjugation via click chemistry, though it may not be the optimal choice for state-of-the-art smFRET applications compared to other UAAs like propargyllysine.

Technology Process of 4-Azido-L-phenylalanine

There total 8 articles about 4-Azido-L-phenylalanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.0%

(S)-3-(4-azidophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid (33173-55-6) → (S)-methyl 2-amino-3-(4-azidophenyl)propanoate (33173-53-4,1241681-80-0)

Guidance literature:

With potassium hydroxide; In 1,4-dioxane; sulfuric acid; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.joc.8b00270

Reference yield: 64.0%

sodium azide + 4-amino-L-phenylalanine (943-80-6) → (S)-methyl 2-amino-3-(4-azidophenyl)propanoate (33173-53-4,1241681-80-0)

Guidance literature:

4-amino-L-phenylalanine; With hydrogenchloride; sodium nitrate; In water; at 0 ℃; for 0.666667h;

sodium azide; In water; at 0 ℃; for 0.0833333h;

DOI:10.3390/molecules18078393

Reference yield:

N-Boc-4-I-Phe-OH (103882-09-3,62129-44-6) → (S)-methyl 2-amino-3-(4-azidophenyl)propanoate (33173-53-4,1241681-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium hydroxide / ethyl acetate / 0 h / 0 °C

1.2: 65 °C / Inert atmosphere

1.3: 24 h / 20 °C / Inert atmosphere

2.1: potassium hydroxide / sulfuric acid; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere

With potassium hydroxide; In 1,4-dioxane; sulfuric acid; ethyl acetate;

DOI:10.1021/acs.joc.8b00270

upstream raw materials:

L-phenylalanine

4-amino-L-phenylalanine

4-nitro-3-phenyl-L-alanine

4-iodo-L-phenylalanine

Refernces

Click strategies for single-molecule protein fluorescence

10.1021/ja210587q

The study systematically investigates various clickable UAAs for their potential in high-resolution smFRET, focusing on parameters such as probe accessibility, protein expression yield, and quantitative labeling. The researchers found that genetically encoding propargyllysine (UAA 5) offers significant advantages for state-of-the-art measurements compared to other UAAs. Using this optimized system, they presented a biocompatible one-step dual-labeling strategy for the regulatory protein RanBP3, demonstrating that a region with two FxFG repeat sequences adopts a disordered but collapsed state. Key chemicals used in the process include UAAs such as p-acetylphenylalanine (1), p-azidophenylalanine (2), p-(propargyloxy)-phenylalanine (3), and aliphatic alkyne UAAs (4 and 5), as well as fluorescent dyes like Alexa 488 and Alexa 594 for labeling and smFRET measurements.