3-Azido-L-alanine HCl

Product Information

Precise and Bioorthogonal Protein Labeling for Advanced Molecular Engineering

3-Azido-L-alanine hydrochloride ((S)-2-Amino-3-azidopropanoic acid hydrochloride) is a synthetic L-alanine derivative featuring an azide group for site-specific protein modification. It can be incorporated into peptides or proteins via:

• Genetic Code Expansion: Using engineered tRNAs (based on prokaryotic tRNAs) that recognize specific amber codons (UAG or UAA), 3-Azido-L-alanine is introduced during peptide biosynthesis at a defined position.
• Solid Phase Peptide Synthesis (SPPS): Enables chemical incorporation at any position in the sequence.

Once incorporated, the azide group allows highly selective labeling through:

• Click Chemistry: SPAAC (strain-promoted) or CuAAC (copper-catalyzed)
• Staudinger Ligation with P(III)-containing reagents

This approach ensures bioorthogonal reactions under mild conditions, preserving protein integrity and avoiding side reaction.

Why buy 3-Azido-L-alanine from baseclick?

• Market-leading pricing with bulk options, ≥ 98% HPLC purity, and reliable supply for research workflows.
• Available Size: 100 mg. Bulk quantities upon request (research use only; not for diagnostic procedures).

What makes 3-Azido-L-alanine different?

Traditional peptide/protein labeling relies on NHS ester chemistry, which reacts with nucleophiles such as every primary amine available. This leads to:

• Non-specific labeling at multiple sites (e.g., lysines)
• Requires basic pH (8–9) and overnight reactions
• Risks protein degradation and structural changes

In contrast, azide-based labeling with 3-Azido-L-alanine offers:

• Site-specific modification at the defined codon
• Fast reactions at neutral pH with high yields
• Preserves tertiary structure
• Fully biorthogonal, meaning no side reactions with native functional groups

How does it work?

3-Azido-L-alanine is introduced during peptide biosynthesis or solid-phase peptide synthesis (SPPS). The azide group reacts with alkyne-modified partners (e.g., alkyne, or DBCO or BCN modified PEGs, dyes, etc.) via click chemistry. Alternative labeling with P(III) reagents via Staudinger ligation is also possible, enabling efficient and selective conjugation without side reactions.

Applications

3-Azido-L-alanine is the ideal reagent for protein and peptide labeling, enabling precise site-specific modification through bioorthogonal click chemistry. It supports antibody modification and ADC synthesis, allowing researchers to create targeted therapeutics with high efficiency. This versatile amino acid derivative is also perfect for linking targeting moieties to proteins for drug delivery or diagnostic applications. Additionally, it serves as a reliable building block for solid-phase peptide synthesis, offering flexibility for custom peptide design in pharmaceutical development and biotechnology research.

LITERATURE

Mapping the Ligand-Binding Site on a G Protein-Coupled Receptor (GPCR) Using Genetically Encoded Photocrosslinkers, Grunbeck et al., 2011, Biochemistry, Vol. 50, p. 3411-3413.

https://doi.org/10.1021/bi200214r

Potent In Vitro Peptide Antagonists of the Thrombopoietin Receptor as Potential Myelofibrosis Drugs, M. Szabo et al., 2021, Advanced Therapeutics, Vol. 4(3), 2000241.

https://doi.org/10.1002/adtp.202000241

Redirecting RiPP Biosynthetic Enzymes to Proteins and Backbone-Modified Substrates, J. A. Walker et al., 2022, ACS Cent. Sci., Vol. 8(4), p. 473–482.

https://doi.org/10.1021/acscentsci.1c01577

Mutagenicity of 3-azido-1,2-propanediol and 9-(3-azido-2-hydroxypropyl)-adenine in repair deficient strains of Escherichia coli, P. Grúz et al., 1993, Mutation Research Letters, Vol. 303(1), p. 1-9.

https://doi.org/10.1016/0165-7992(93)90002-D