H-γ-azido-Abu-OH

 CAS No.: 120042-14-0  Cat No.: BP-501124  Purity: ≥95% 4.5  

H-γ-azido-Abu-OH is a protected-free, functionalized amino acid building block featuring a γ-position azide handle on an alanine-derived backbone (β/γ-amino acid motif) that can be used to introduce an orthogonal conjugation site into PROTAC linkers. The azide group enables bioorthogonal “click” chemistry, most commonly copper(I)-catalyzed azide–alkyne cycloaddition or strain-promoted azide–alkyne cycloaddition, allowing researchers to connect this linker fragment to complementary alkyne-bearing moieties such as warhead or E3-ligase ligands. In PROTAC architectures, this linkage strategy supports modular synthesis, enabling systematic tuning of linker length, geometry, and attachment points while preserving the chemical integrity of sensitive ligand pharmacophores. As a versatile handle for late-stage assembly, H-γ-azido-Abu-OH is valuable for constructing degraders that require precise, chemoselective conjugation and for generating structure–activity relationship libraries in targeted protein degradation research.

H-γ-azido-Abu-OH

Structure of 120042-14-0

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Category
PROTAC Linker
Molecular Formula
C4H8N4O2
Molecular Weight
144.13
Related CAS
<a href="/product/n-azido-l-2-4-diaminobutyric-acid-cas-942518-29-8-156377.html">942518-29-8</a> (monohydrochloride)
Appearance
Off-white Solid

* For research and manufacturing use only. Not for human or clinical use.

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Purity
≥95%
Solubility
Soluble in Water
Appearance
Off-white Solid
Application
A novel mutagenic amino acid.
Storage
Store at -20°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
(2S)-2-amino-4-azidobutanoic acid
Synonyms
L-Azidohomoalanine HCl salt;H-Dab(N2)-OH; L-γ-azidohomoalanine; H-γ-Aha-OH; (2S)-4-azido-2-aminobutyric acid; H-Abu(N3)-OH; L-Azidohomoalanine; (S)-2-Amino-4-azidobutanoic acid; 4-Azido-L-2-aminobutyrate; L-2-Amino-4-azidobutanoic acid
Melting Point
220-223°C
InChI Key
NNWQLZWAZSJGLY-VKHMYHEASA-N
InChI
InChI=1S/C4H8N4O2/c5-3(4(9)10)1-2-7-8-6/h3H,1-2,5H2,(H,9,10)/t3-/m0/s1
SMILES
C(CN=[N+]=[N-])C(C(=O)O)N

H-γ-azido-Abu-OH, provides a chemically versatile handle for constructing targeted protein degraders via modular conjugation strategies. Its azide functionality enables bioorthogonal coupling to complementary partners, supporting efficient assembly of PROTAC architectures while preserving linker integrity and minimizing undesired side reactions. The structural features and reactivity profile make it well suited for linker-to-ligand and linker-to-warhead attachment workflows, as described in established PROTAC and click-chemistry methodologies. Detailed structural and reactivity considerations are provided below.

Structure: H-γ-azido-Abu-OH is an amino acid derivative bearing a terminal azide group on the γ-position and a free carboxylic acid. It contains an aliphatic backbone with amine and carboxyl functionalities, along with an azide substituent suitable for selective cycloaddition chemistry.

Reactivity: The azide group is typically engaged in copper-catalyzed azide–alkyne cycloaddition or related azide-based conjugation schemes with appropriately functionalized alkynes or azide-compatible partners. PROTAC assembly commonly proceeds under inert or controlled atmospheres using standard click-chemistry solvents and base additives, with copper catalysts and ligand systems selected to balance reaction rate and stability. Protecting-group strategies for the amino and carboxyl groups are often used to ensure chemoselective coupling during linker installation.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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