Boc-Gly-amido-C-PEG3-C3-amine

 CAS No.: 525583-49-7  Cat No.: BP-500417 4.5  

Boc-Gly-amido-C-PEG3-C3-amine is a protected, amide-linked PEG-based linker designed for modular PROTAC synthesis. Structurally, it combines a Boc-protected glycine-derived amide segment with a short, flexible triethylene glycol (PEG3) spacer and a terminal primary amine, enabling straightforward coupling to electrophilic warheads or ligands and subsequent conjugation to the complementary binding module. The PEG3 chain provides conformational flexibility and aqueous solubility, which can improve productive spatial positioning of the two recruited proteins and reduce steric mismatch at the ternary complex interface. In PROTAC design, this linker functions as a “molecular ruler” that tunes distance and relative orientation between the target-binding ligand and the E3-ligase recruiting element, thereby influencing ubiquitination efficiency and degradation potency. Its amine handle supports efficient amide formation or other standard derivatization steps, making it valuable for rapid linker optimization and systematic structure–activity relationship studies in targeted protein degradation research.

Boc-Gly-amido-C-PEG3-C3-amine

Structure of 525583-49-7

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PROTAC Linker
Molecular Formula
C₁₇H₃₅N₃O₆
Molecular Weight
377.48

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

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IUPACName
tert-butyl N-[2-[3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propylamino]-2-oxoethyl]carbamate
InChI Key
LRMUHZCCKYZFHS-UHFFFAOYSA-N
InChI
InChI=1S/C17H35N3O6/c1-17(2,3)26-16(22)20-14-15(21)19-7-5-9-24-11-13-25-12-10-23-8-4-6-18/h4-14,18H2,1-3H3,(H,19,21)(H,20,22)
SMILES
CC(C)(C)OC(=O)NCC(=O)NCCCOCCOCCOCCCN

Boc-Gly-amido-C-PEG3-C3-amine, is designed to provide a chemically versatile, PEG-enabled spacer for assembling targeted protein degraders. Its functional handles support robust conjugation strategies to connect ligands while maintaining favorable solubility and conformational flexibility. The subsequent sections describe the linker’s structural features and practical reactivity considerations for PROTAC construction, enabling researchers to tailor linker length, attachment chemistry, and coupling efficiency for their specific E3 ligase and target ligand pairings.

Structure: The linker contains a Boc-protected glycinamide motif and a PEG-based spacer, providing ether-rich segments that enhance hydrophilicity. It incorporates amide and carbamate functionalities alongside terminal amine functionality, enabling stable amide bond formation and controlled deprotection chemistry under standard organic conditions.

Reactivity: Suitable PROTAC assembly typically relies on orthogonal functional group interconversions: Boc deprotection to reveal the primary amine, followed by coupling to carboxyl- or activated ester–containing ligand fragments to form amide bonds. Common approaches use carbodiimide-mediated coupling with appropriate bases in polar aprotic solvents, or activated ester chemistry, proceeding via nucleophilic acyl substitution. Protecting-group compatibility and solvent choice are important for maintaining linker integrity during sequential steps.

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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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