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H-L-Tyr(2-azidoethyl)-OH

  CAS No.: 1570523-47-5   Cat No.: BADC-01833 4.5  

H-L-Tyr(2-azidoethyl)-OH is an azide-functionalized tyrosine ADC linker intermediate enabling copper-free click chemistry for site-specific antibody conjugation, enhancing antibody-drug conjugate stability and targeted therapy.

H-L-Tyr(2-azidoethyl)-OH

Structure of 1570523-47-5

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ADC Linker
Molecular Formula
C11H14N4O3
Molecular Weight
250.25

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Synonyms
4-(2-Azidoethoxy)-L-phenylalanine
IUPAC Name
(2S)-2-amino-3-[4-(2-azidoethoxy)phenyl]propanoic acid
Canonical SMILES
C1=CC(=CC=C1CC(C(=O)O)N)OCCN=[N+]=[N-]
InChI
InChI=1S/C11H14N4O3/c12-10(11(16)17)7-8-1-3-9(4-2-8)18-6-5-14-15-13/h1-4,10H,5-7,12H2,(H,16,17)/t10-/m0/s1
InChIKey
AFRGRMSRGXONSC-JTQLQIEISA-N

H-L-Tyr(2-azidoethyl)-OH, a modified amino acid with exceptional properties, finds versatile applications in various scientific contexts. Here are four key applications:

Click Chemistry: H-L-Tyr(2-azidoethyl)-OH serves as a pivotal component for bioconjugation and labeling purposes. The azido group attached to this specialized tyrosine derivative acts as a crucial anchor for coupling with alkyne-containing molecules through a copper-catalyzed azide-alkyne cycloaddition reaction. This facilitates precise modifications of proteins, peptides, and other biomolecules, catering to diverse research and diagnostic needs.

Protein Engineering: Within the domain of protein engineering, H-L-Tyr(2-azidoethyl)-OH plays a transformative role by allowing for site-specific modifications in proteins. By substituting natural tyrosine with this modified form, researchers can seamlessly attach a myriad of functional groups or probes to the protein structure. This technique proves invaluable for in-depth investigations into protein structure, function, and intricate interactions.

Peptide Synthesis: H-L-Tyr(2-azidoethyl)-OH enables the creation of peptides with designated labeling or functionalization sites. The azido group presents a selective target for conjugation with fluorescent dyes, affinity tags, or other chemical entities, facilitating the generation of highly specialized peptides tailored for biochemical assays, imaging studies, and therapeutic applications.

Bioorthogonal Reactions: The azido group integrated into H-L-Tyr(2-azidoethyl)-OH serves as a fundamental asset in bioorthogonal reactions, which are instrumental for conducting chemical processes within living systems without disrupting native biochemical pathways. This unique property allows for selective labeling and tracking of biomolecules within complex biological milieus, empowering researchers to explore cellular localization, protein dynamics, and molecular interactions in vivo with a precision that was previously unattainable.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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