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3-Azido-N-Boc-D-Alanine

  CAS No.: 225780-77-8   Cat No.: BADC-01950 4.5  

3-Azido-N-Boc-D-Alanine is a protected azide-functionalized amino acid used in ADC linker chemistry. Its azide moiety allows copper-free click conjugation, supporting site-selective payload attachment and improving conjugate homogeneity and therapeutic index in ADCs.

3-Azido-N-Boc-D-Alanine

Structure of 225780-77-8

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ADC Linker
Molecular Formula
C8H14N4O4
Molecular Weight
230.22

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Synonyms
Boc-D-Aza-OH; 3-Azido-N-[(1,1-dimethylethoxy)carbonyl]-D-alanine; N-Tert-butoxycarbonyl-azido-D-alanine
IUPAC Name
(2R)-3-azido-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Canonical SMILES
CC(C)(C)OC(=O)NC(CN=[N+]=[N-])C(=O)O
InChI
InChI=1S/C8H14N4O4/c1-8(2,3)16-7(15)11-5(6(13)14)4-10-12-9/h5H,4H2,1-3H3,(H,11,15)(H,13,14)/t5-/m1/s1
InChIKey
KIFVOLVBGXELHT-RXMQYKEDSA-N

3-Azido-N-Boc-D-Alanine, a versatile chemical compound with diverse applications in biochemical and pharmaceutical research, showcases high perplexity and burstiness in its key applications:

Peptide Synthesis: Widely integrated into peptide synthesis, 3-Azido-N-Boc-D-Alanine acts as a pivotal building block in solid-phase synthesis, enabling the introduction of azido functional groups. This is crucial for applications of click chemistry, where azide-alkyne cycloaddition is employed to connect peptide chains through varied lengths, contributing to the multifaceted complexity of peptide structures and functionality.

Drug Discovery: Within the realm of pharmaceutical research, 3-Azido-N-Boc-D-Alanine plays a pivotal role in the development of innovative therapeutics. Its azido component readily conjugates with diverse bioactive molecules, aiding in the screening and identification of potential drug candidates. This compound serves as a significant tool in constructing compound libraries for high-throughput drug screening initiatives, leading to a burst of possibilities in discovering novel drug solutions.

Protein Labeling: Researchers harness the potential of 3-Azido-N-Boc-D-Alanine for precise site-specific labeling of proteins and biomolecules. The selective attachment of the azido group to fluorescent dyes or affinity tags through click chemistry empowers the analysis of protein dynamics, interactions, and localization within cellular environments. This sophisticated approach enriches our comprehension of protein functionality and navigates the intricate landscape of cellular mechanisms with an exquisite blend of complexity and variation.

Chemical Biology: In the domain of chemical biology, 3-Azido-N-Boc-D-Alanine serves as a crucial component for probing and manipulating biological pathways. It acts as a foundational element for generating bioorthogonal probes and sensors, offering real-time tracking capabilities for monitoring cellular processes. This innovative methodology is indispensable for unraveling the intricate web of biological interactions and designing targeted molecular interventions with a rich tapestry of complexity and intricacy.

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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