4-Azido-L-phenylalanine Chemical Properties

storage temp. 

-20°C

solubility 

Water : 6.2 mg/mL (30.07 mM; ultrasonic and adjust pH to 6 with HCl);DMSO : 6 mg/mL (29.10 mM; ultrasonic and adjust pH to 6 with HCl)

form 

Solid

color 

White to yellow

Appearance

off-white solid

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)/t8-/s3

InChIKey

NEMHIKRLROONTL-SBYBRXNCNA-N

SMILES

C(C1C=CC(N=[N+]=[N-])=CC=1)[C@H](N)C(=O)O |&1:10,r|

Safety Information

HS Code 

2922498590

4-Azido-L-phenylalanine Usage And Synthesis

Description

4-Azido-L-phenylalanine (4AZP) is an unnatural amino acid analog of L-phenylalanine that contains an azide moiety. 4AZP-labeling is a fast, sensitive, and non-radioactive alternative to the traditional technique for detecting nascent protein synthesis.

4AZP is randomly incorporated into synthesizing protein instead of phenylalanine during translation. The resulting azide-labeled full-length proteins can be detected via copper-catalyzed click reaction (with fluorescent or biotin-labeled alkynes) or copper-free click reaction (with cycloalkynes) and used for subsequent microscopic imaging or purification tasks.

Chemical Properties

Off-white to brown powder

Uses

4-Azido-L-phenylalanine is an unnatural derivative of L-phenylalanine. It is a nonpolar, essential amino acid that naturally occurs in the human body and is also used to treat patients with depression.

Uses

The in-vivo incorporation of clickable unnatural amino acids such as 4-Azido-L-phenylalanine with unique reactivity at a defined postition is used for functionalization of proteins. The azide functionalities in the protein can then be modified with almost any alkyne bearing molecule by Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC). Copper-free alternatives with strained internal alkynes are also available (SPAAC). Some examples enabled with this technique are protein PEGylation, masking with sugars, and the attachment to antibodies.

reaction suitability

reaction type: click chemistry
reaction type: solution phase peptide synthesis

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