N-Boc-N-bis(C2-PEG1-azide)

 CAS No.: 2100306-79-2  Cat No.: BP-500698  Purity: 98% 4.5  

N-Boc-N-bis(C2-PEG1-azide) is a protected, bis-functional polyethylene glycol (PEG) linker bearing azide termini and a Boc-protected central amine. Structurally, it provides a short, flexible C2-PEG1 chain length on each arm, enabling controlled spatial separation between two conjugation sites while maintaining solubility and reducing nonspecific interactions. In PROTAC and targeted protein degradation workflows, the azide groups serve as convenient handles for orthogonal “click” chemistry (typically copper-catalyzed or strain-promoted azide–alkyne cycloaddition) to attach two different PROTAC fragments, such as a ligand for an E3 ubiquitin ligase and a ligand for the target protein, or to incorporate additional functional motifs (e.g., solubilizing groups or reporter tags). The Boc protection supports practical synthesis and purification by stabilizing the amine during assembly steps. This linker is valuable for researchers optimizing linker length, geometry, and conjugation efficiency to tune ternary complex formation and degradation potency.

N-Boc-N-bis(C2-PEG1-azide)

Structure of 2100306-79-2

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Category
PROTAC Linker
Molecular Formula
C₁₃H₂₅N₇O₄
Molecular Weight
343.38

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

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Purity
98%
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
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Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl N,N-bis[2-(2-azidoethoxy)ethyl]carbamate
Synonyms
N-Boc-N-bis(PEG1-azide)
InChI Key
HGPOSUHEHQKFBQ-UHFFFAOYSA-N
InChI
InChI=1S/C13H25N7O4/c1-13(2,3)24-12(21)20(6-10-22-8-4-16-18-14)7-11-23-9-5-17-19-15/h4-11H2,1-3H3
SMILES
CC(C)(C)OC(=O)N(CCOCCN=[N+]=[N-])CCOCCN=[N+]=[N-]

N-Boc-N-bis(C2-PEG1-azide), is designed to provide a flexible polyethylene glycol spacer terminating in azide groups, enabling modular conjugation to targeting ligands and E3-recruiting moieties. Its PEG-based architecture supports productive ternary complex formation by improving solubility and conformational adaptability, while the azide handles enable reliable “click” coupling strategies. Detailed structural and synthetic considerations are provided below to support experimental PROTAC assembly.

Structure: The molecule contains a Boc-protected nitrogen center and two PEG-derived arms terminating in azide functional groups. It features ether linkages within the PEG segments, along with carbamate character from the Boc group. The presence of azides provides defined, bioorthogonal reactive termini, and the PEG framework imparts hydrophilicity and conformational flexibility.

Reactivity: The azide termini are well suited for copper-catalyzed azide–alkyne cycloaddition or strain-promoted azide–alkyne cycloaddition, allowing efficient formation of stable triazole linkages to alkyne-bearing partners. Typical coupling is performed under conditions compatible with PEG-containing intermediates, using appropriate base and catalyst systems for CuAAC or catalyst-free conditions for SPAAC. Reaction progress is commonly monitored by chromatographic methods, and purification can be optimized to remove residual catalyst or small-molecule byproducts.

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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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