t-Boc-N-amido-PEG9-azide

 CAS No.: 2112731-50-5  Cat No.: BP-500907  Purity: >97% 4.5  

t-Boc-N-amido-PEG9-azide is a polyethylene glycol (PEG) linker functionalized with a terminal azide group and an N-amide bearing a tert-butoxycarbonyl (t-Boc) protecting group. The PEG segment provides a flexible, hydrophilic spacer of defined length, which helps reduce steric interference between the two binding partners in PROTAC constructs and can improve solubility and effective reach during ternary complex formation. The azide handle enables efficient bioorthogonal conjugation, most commonly via copper-free azide–alkyne cycloaddition or related click chemistries, allowing researchers to attach the linker to complementary PROTAC modules such as ligands or reactive warheads bearing an appropriate alkyne or other azide-compatible functionality. In targeted protein degradation research, this linker is valuable for modular assembly of degraders, facilitating systematic optimization of linker length and attachment geometry to tune degradation potency and selectivity in cellular assays.

t-Boc-N-amido-PEG9-azide

Structure of 2112731-50-5

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Category
PROTAC Linker
Molecular Formula
C₂₅H₅₀N₄O₁₁
Molecular Weight
582.68

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

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Purity
>97%
Solubility
Water, DMSO, DCM, DMF
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl N-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl]carbamate
Synonyms
BocNH-PEG9-CH2CH2N3
InChI Key
CKIKYHBSXHEGSA-UHFFFAOYSA-N
InChI
InChI=1S/C25H50N4O11/c1-25(2,3)40-24(30)27-4-6-31-8-10-33-12-14-35-16-18-37-20-22-39-23-21-38-19-17-36-15-13-34-11-9-32-7-5-28-29-26/h4-23H2,1-3H3,(H,27,30)
SMILES
CC(C)(C)OC(=O)NCCOCCOCCOCCOCCOCCOCCOCCOCCOCCN=[N+]=[N-]

t-Boc-N-amido-PEG9-azide is a polyethylene glycol–based PROTAC linker building block designed to introduce a protected amide functionality together with a terminal azide handle for modular conjugation. Its PEG-rich scaffold enhances linker solubility and conformational flexibility, which can improve productive ternary complex formation in targeted protein degradation workflows. The following sections describe the molecule’s structure and the practical reactivity considerations for constructing PROTACs using this linker.

Structure: The linker comprises a PEG oligomer segment bearing an N-amido linkage and a terminal azide group, with a t-Boc protecting group on the nitrogen. It contains ether linkages in the PEG chain, amide and carbamate functionalities, and an azide moiety suitable for bioorthogonal coupling. Overall, it is typically water-compatible and chemically stable under standard handling.

Reactivity: The azide enables azide–alkyne cycloaddition (Cu(I)-catalyzed or copper-free variants) for installing protein-binding warheads or E3 ligands via an alkyne partner. The t-Boc group can be removed under acid-promoted conditions to reveal the amine for subsequent amide-forming coupling. Suitable solvents include polar aprotic media for coupling steps and aqueous/organic mixtures for click reactions, with catalysts selected to balance efficiency and azide stability.

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* Our calculator is based on the following equation:
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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