t-Boc-Aminooxy-PEG3-azide

 CAS No.: 1235514-15-4  Cat No.: BP-501266  Purity: ≥95% 4.5  

t-Boc-Aminooxy-PEG3-azide is a protected aminooxy-functionalized polyethylene glycol linker comprising an ether-based PEG chain of three repeating units and a terminal azide handle suitable for bioorthogonal conjugation. The t-Boc group masks the aminooxy functionality during synthesis, while deprotection enables formation of stable oxime or related oxime-derivative linkages with carbonyl-bearing targeting ligands, a common strategy in PROTAC construction to connect a targeting moiety to the degradation module without introducing reactive amines. In PROTAC designs, this linker provides controlled spatial separation and aqueous solubility, helping to tune the effective reach and orientation between the ligand that recruits an E3 ligase and the ligand that binds the target protein. The azide group enables efficient attachment via copper-free azide–alkyne cycloaddition or azide-based coupling to complementary fragments, facilitating modular assembly and rapid structure–activity optimization in targeted protein degradation research.

t-Boc-Aminooxy-PEG3-azide

Structure of 1235514-15-4

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Category
PROTAC Linker
Molecular Formula
C13H26N4O6
Molecular Weight
334.37
Appearance
Solid Powder

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

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Purity
≥95%
Solubility
Soluble in DMSO
Appearance
Solid Powder
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl N-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]carbamate
Synonyms
Boc-Aminooxy-PEG3-azide; t-Boc-Aminoxy-PEG3-Azide; tert-butyl (2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethoxy)carbamate; Boc-Aminoxy-PEG3-N3; Boc-Aminoxy-PEG3-N3; 2-Methyl-2-propanyl (2-{2-[2-(2-azidoethoxy)ethoxy]ethoxy}ethoxy)carbamate; Carbamic acid, N-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]-, 1,1-dimethylethyl ester
InChI Key
NMMKIEUJNULAEQ-UHFFFAOYSA-N
InChI
InChI=1S/C13H26N4O6/c1-13(2,3)23-12(18)16-22-11-10-21-9-8-20-7-6-19-5-4-15-17-14/h4-11H2,1-3H3,(H,16,18)
SMILES
CC(C)(C)OC(=O)NOCCOCCOCCOCCN=[N+]=[N-]

t-Boc-Aminooxy-PEG3-azide is a PEG-based, bifunctional linker designed for assembling PROTACs through orthogonal chemistries that connect targeting ligands and enable controlled spatial presentation to the recruited E3 ligase. Its protected aminooxy handle supports selective coupling strategies, while the azide provides a versatile bioorthogonal “click” handle for modular conjugation. The combination of PEG flexibility and functional-group compatibility can improve linker solubility and facilitate systematic PROTAC optimization; detailed structural and reactivity considerations are provided below.

Structure: The linker contains a protected aminooxy moiety and an azide functional group separated by a short poly(ethylene glycol) segment. It features ether linkages characteristic of PEG, an azide-bearing carbon framework, and a tert-butoxycarbonyl-protected aminooxy functionality, supporting stable handling and selective downstream functionalization.

Reactivity: The azide group is well suited for copper-catalyzed azide–alkyne cycloaddition or strain-promoted azide–alkyne cycloaddition, enabling modular attachment of complementary alkyne partners under mild, aqueous-compatible conditions. The aminooxy group can participate in oxime-formation or related aminooxy coupling workflows after deprotection, typically using electrophiles such as aldehydes under controlled pH. Orthogonal protection and sequential coupling are commonly used to preserve chemoselectivity without cross-reactivity.

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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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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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