BCN-POE3-amine

 CAS No.: 1263166-93-3  Cat No.: BP-501582  Purity: >99% 4.5  

BCN-POE3-amine is a bicyclononyne (BCN)–functionalized poly(ethylene glycol) linker bearing a terminal primary amine, designed for copper-free strain-promoted azide–alkyne cycloaddition (SPAAC) conjugation in targeted protein degradation workflows. Structurally, it comprises a BCN cyclooctyne-like reactive handle connected through a short, flexible ethylene glycol chain of three repeat units to an amine terminus, providing both aqueous compatibility and a convenient site for subsequent coupling to degraders, ligands, or linker fragments. In PROTAC construction, the BCN moiety enables rapid, bioorthogonal attachment to azide-bearing components, allowing assembly of multicomponent systems without metal catalysts that can interfere with sensitive reagents or biological assays. The terminal amine further supports derivatization (e.g., amide or urea formation) to tune linker length, polarity, and spatial presentation. This reagent is valuable for researchers seeking modular, efficient conjugation strategies to generate and optimize PROTACs and related targeted degradation probes.

BCN-POE3-amine

Structure of 1263166-93-3

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Category
PROTAC Linker
Molecular Formula
C₁₇H₂₈N₂O₄
Molecular Weight
324.42
Appearance
Transparent Liquid

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

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Purity
>99%
Appearance
Transparent Liquid
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
[(1R,8S)-9-bicyclo[6.1.0]non-4-ynyl]methyl N-[2-[2-(2-aminoethoxy)ethoxy]ethyl]carbamate
Synonyms
N-(1R,8S,9S)-Bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl-1,8-diamino-3,6-dioxaoctane
InChI Key
YZGOWXGENSKDSE-XYPWUTKMSA-N
InChI
InChI=1S/C17H28N2O4/c18-7-9-21-11-12-22-10-8-19-17(20)23-13-16-14-5-3-1-2-4-6-15(14)16/h14-16H,3-13,18H2,(H,19,20)/t14-,15+,16?
SMILES
C1CC2C(C2COC(=O)NCCOCCOCCN)CCC#C1

BCN-POE3-amine is a BCN-based, amine-terminated polyethylene glycol linker designed for efficient incorporation into PROTAC architectures. Its cyclooctyne motif supports bioorthogonal conjugation, while the flexible POE segment helps tune linker length, solubility, and conformational freedom between the target-binding ligand and the recruited E3 ligase module. This product is particularly useful for constructing degraders where robust, selective coupling chemistry and favorable physicochemical properties are required; detailed structural and reactivity considerations are provided below.

Structure: BCN-POE3-amine contains a bicyclononyne (BCN) reactive cyclooctyne core connected to a polyethylene oxide (POE) chain terminating in a primary amine. The molecule features an amine-bearing linker with ether-rich segments, enabling hydrogen bonding and improved aqueous compatibility.

Reactivity: BCN-POE3-amine is suited for strain-promoted azide–alkyne cycloaddition (SPAAC) with azide-functional partners under mild, catalyst-free conditions. For PROTAC assembly, the amine handle can be used for standard amide or urea-forming coupling strategies with activated carboxylic acid derivatives. Typical workflows employ aqueous or mixed aqueous/organic solvents and rely on maintaining azide and BCN integrity, avoiding strongly nucleophilic or reducing conditions that could compromise functional groups.

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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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