N-(Azido-PEG3)-N-Boc-PEG3-t-butyl ester

 CAS No.: 2112732-03-1  Cat No.: BP-500976  Purity: 98% 4.5  

N-(Azido-PEG3)-N-Boc-PEG3-t-butyl ester is a heterobifunctional polyethylene glycol (PEG) linker featuring two PEG3 segments and a terminal azide handle alongside a protected carboxylate functionality. Structurally, it provides an azide-bearing PEG spacer for bioorthogonal conjugation (commonly via azide–alkyne cycloaddition to install or exchange targeting ligands) while the Boc-protected amine and t-butyl ester enable controlled stepwise synthesis and purification of PROTAC intermediates. In PROTAC design, this linker serves to spatially separate the target-binding and E3-ligase-binding modules, improving productive ternary complex formation by reducing steric clashes and increasing effective reach. Its PEG-rich architecture also enhances solubility and can mitigate aggregation during linker-ligand assembly. For targeted protein degradation research, it is valuable for modular synthesis of degraders and for rapid diversification of linker length and attachment chemistry while maintaining chemically defined attachment points for subsequent coupling.

N-(Azido-PEG3)-N-Boc-PEG3-t-butyl ester

Structure of 2112732-03-1

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Category
PROTAC Linker
Molecular Formula
C₂₆H₅₀N₄O₁₀
Molecular Weight
578.70

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

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Popular Publications Citing BOC Sciences Products
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 3-[2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
tert-butyl 3-(2-{2-[2-(16-azido-2,2-dimethyl-4-oxo-3,8,11,14-tetraoxa-5-azahexadecan-5-yl)ethoxy]ethoxy}ethoxy)propanoate
InChI Key
IZIWQDDVTKZAPK-UHFFFAOYSA-N
InChI
InChI=1S/C26H50N4O10/c1-25(2,3)39-23(31)7-11-33-15-19-37-21-17-35-13-9-30(24(32)40-26(4,5)6)10-14-36-18-22-38-20-16-34-12-8-28-29-27/h7-22H2,1-6H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCN(CCOCCOCCOCCN=[N+]=[N-])C(=O)OC(C)(C)C
1. Notch Signaling Mediates Radiation-Induced Smooth Muscle Cell Hypermuscularization and Cerebral Vasculopathy
Yuhua Yang, Honghong Li, Yongteng Xu, Jiatian Xie, Qiang Liu, Zhongshan Shi, Jialin Huang, Jinping Cheng, Siqi Chen, Sitai Chen, Xiaohui Zhao, Shaojian Li, Zhan Zhang, Jinhua Cai, Baixuan He, Wei-Jye Lin, Qingyu Shen, Yi Li, Yamei Tang Stroke. 2022 Dec;53(12):3751-3762.doi: 10.1161/STROKEAHA.122.040697.Epub 2022 Oct 28.
Background:Emerging evidence highlighted vascular injury in aggravating radiation-induced brain injury (RIBI), a common complication of radiotherapy. This study aimed to delineate the pathological feature of cerebral small vessel and investigate the functional roles of Notch signaling in RIBI.

This linker is designed for modular PROTAC assembly by providing an azide handle for orthogonal conjugation and PEG-based spacing to support productive ternary complex formation. Its PEG-rich architecture offers hydrophilicity and conformational flexibility, which can improve solubility and reduce non-specific interactions during targeted protein degradation workflows. The following sections describe its structural attributes and practical reactivity considerations for constructing PROTACs in a stepwise, researcher-friendly manner.

Structure: The molecule contains an azido-functional group and PEG segments, connected through ether linkages that confer flexibility and water-compatible character. A Boc-protected amine and a t-butyl ester are present, enabling controlled functional group interconversions. These features support orthogonal coupling strategies typical of PROTAC linker design.

Reactivity: The azide group is well-suited to copper-catalyzed azide–alkyne cycloaddition or strain-promoted azide–alkyne ligation, enabling attachment to complementary warheads or E3 ligands under bioorthogonal conditions. The Boc protecting group can be removed using standard acidolysis conditions to reveal an amine for subsequent carbamate or amide formation. The t-butyl ester can be cleaved under acid to generate a carboxylic acid for coupling reactions, commonly using activated ester or coupling reagent chemistries in polar organic solvents with appropriate bases.

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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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