endo-BCN-PEG2-acid

 CAS No.: 1993134-72-7  Cat No.: BP-501595  Purity: 95% 4.5  

Endo-BCN-PEG2-acid is a bifunctional, BCN (bicyclo[6.1.0]nonyne)–containing polyethylene glycol linker bearing a terminal carboxylic acid. Structurally, it combines a strained cyclooctyne handle for rapid strain-promoted azide–alkyne cycloaddition (SPAAC) with a short PEG spacer that provides aqueous solubility and spatial separation between conjugated partners. In PROTAC design, this linker is used to connect a targeting ligand (or other functional module) to a second component such as an E3 ligase binder or a reporter/handle via azide-bearing intermediates, enabling copper-free conjugation under mild conditions. The PEG2 segment helps reduce steric interference at the binding interfaces and can improve effective local concentration of the assembled degrader. As a modular coupling reagent, it supports systematic optimization of linker length and attachment chemistry, facilitating efficient synthesis and comparative evaluation of targeted protein degradation constructs in biochemical and cellular studies.

endo-BCN-PEG2-acid

Structure of 1993134-72-7

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Category
PROTAC Linker
Molecular Formula
C₁₈H₂₇NO₆
Molecular Weight
353.41

* 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
3-[2-[2-[[(1S,8R)-9-bicyclo[6.1.0]non-4-ynyl]methoxycarbonylamino]ethoxy]ethoxy]propanoic acid
Synonyms
3-(2-{2-[({[(1R,8S,9S)-bicyclo[6.1.0]non-4-yn-9-yl]methoxy}carbonyl)amino]ethoxy}ethoxy)propanoic acid; 3-[2-[2-[[(1R,8S)-9-bicyclo[6.1.0]non-4-ynyl]methoxycarbonylamino]ethoxy]ethoxy]propanoic acid
InChI Key
IAUAMLUNAMJRHF-XYPWUTKMSA-N
InChI
InChI=1S/C18H27NO6/c20-17(21)7-9-23-11-12-24-10-8-19-18(22)25-13-16-14-5-3-1-2-4-6-15(14)16/h14-16H,3-13H2,(H,19,22)(H,20,21)/t14-,15+,16?
SMILES
C1CC2C(C2COC(=O)NCCOCCOCCC(=O)O)CCC#C1

Endo-BCN-PEG2-acid is a bifunctional PEG-based linker designed for constructing PROTACs that require efficient conjugation and controlled spatial presentation of two ligands. Its endo-bicyclononyne (BCN) reactivity enables bioorthogonal coupling, while the PEG spacer and terminal carboxylic acid support robust attachment strategies and improved solubility. The molecule is therefore well suited to targeted protein degradation workflows, where detailed linker structure and coupling guidance are critical for reproducible synthesis and subsequent biological evaluation.

Structure: The linker incorporates an endo-BCN moiety connected through a short polyethylene glycol segment to a terminal carboxylic acid. It contains an alkyne-containing bicyclic framework, ether linkages within the PEG chain, and a carboxylate-forming functional group suitable for amide formation.

Reactivity: BCN-based conjugation is commonly performed via strain-promoted azide–alkyne cycloaddition with azide-bearing partners under mild, catalyst-free conditions. For PROTAC assembly, the terminal carboxylic acid is typically converted to an activated intermediate (for example, using standard coupling reagents) to form amide bonds with amine-functionalized ligands. Reactions are generally carried out in polar organic solvents or buffered aqueous media compatible with azide–BCN coupling, with careful control of pH and ligand 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

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