endo-BCN-PEG4-Boc

 CAS No.: 1807501-83-2  Cat No.: BP-501193  Purity: 95% 4.5  

Endo-BCN-PEG4-Boc is a BCN (bicyclononyne)–functionalized polyethylene glycol linker bearing a tert-butyl ester-protected carboxylic acid handle, designed for bioorthogonal conjugation in targeted protein degradation workflows. Structurally, it combines a cyclooctyne-based BCN moiety with a short, flexible PEG chain that provides aqueous solubility and spatial separation, while the tert-butyl ester can be removed to reveal a carboxylic acid for subsequent activation and coupling. In PROTAC design, the BCN group enables fast, selective strain-promoted azide–alkyne cycloaddition (SPAAC) to connect the linker to azide-tagged ligands or degraders without copper catalysis, preserving sensitive biomolecular components. The PEG4 segment acts as a spacer to tune effective proximity and orientation between the two binding elements, which can improve ternary complex formation and degradation efficiency. This linker is valuable for constructing modular PROTACs and related targeted degradation conjugates, facilitating rapid synthesis and systematic structure–activity studies.

endo-BCN-PEG4-Boc

Structure of 1807501-83-2

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Category
PROTAC Linker
Molecular Formula
C₂₆H₄₃NO₈
Molecular Weight
497.62

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

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Purity
95%
Solubility
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 3-[2-[2-[2-[2-(9-bicyclo[6.1.0]non-4-ynylmethoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
endo-BCN-PEG4-t-butyl ester
InChI Key
BSCLHAMNOSOPKH-UHFFFAOYSA-N
InChI
InChI=1S/C26H43NO8/c1-26(2,3)35-24(28)10-12-30-14-16-32-18-19-33-17-15-31-13-11-27-25(29)34-20-23-21-8-6-4-5-7-9-22(21)23/h21-23H,6-20H2,1-3H3,(H,27,29)
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCOCCNC(=O)OCC1C2C1CCC#CCC2

This endo-BCN-PEG4-Boc linker is designed for modular PROTAC assembly, enabling efficient conjugation of targeting ligands to a PEG-based spacer while incorporating a tert-butyl ester-protected carboxyl handle for controlled downstream functionalization. Its PEG segment supports favorable solubility and reduced steric interference, which can improve the practical performance of assembled degraders. The points below describe its structure and provide guidance on how it can be used in PROTAC construction workflows.

Structure: The linker comprises an endo-bicyclononyne (BCN) cyclooctyne motif connected to a PEG-based spacer and a tert-butyl ester-protected carboxylic acid. It features a strained alkyne suitable for bioorthogonal cycloaddition, ether-rich PEG segments for flexibility, and a tert-butyl ester protecting a carboxylic acid.

Reactivity: The BCN group enables strain-promoted azide–alkyne cycloaddition under catalyst-free, mild conditions, making it compatible with sensitive biomolecule conjugation steps. For PROTAC synthesis, the tert-butyl ester is typically retained during the initial coupling and later deprotected under standard acid-mediated conditions to reveal a carboxylic acid for subsequent amide-forming coupling. Common solvents include polar organic media and aqueous-compatible buffers, chosen to maintain solubility and preserve ligand activity.

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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

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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