N-(PEG2-Boc)-N-bis(PEG2-propargyl)

 CAS No.: 2100306-69-0  Cat No.: BP-500852  Purity: 98% 4.5  

N-(PEG2-Boc)-N-bis(PEG2-propargyl) is a branched polyethylene glycol linker featuring a central tertiary amine bearing three functional arms: a Boc-protected carboxylate and two propargyl-terminated PEG chains. This trifunctional architecture enables sophisticated orthogonal conjugation strategies in PROTAC assembly. The two propargyl groups provide terminal alkynes that serve as bioorthogonal handles for copper-catalyzed azide-alkyne cycloaddition, allowing selective coupling to azide-functionalized target protein ligands or E3 ubiquitin ligase-recruiting moieties. The dual propargyl arms enable the construction of bivalent or multivalent PROTAC architectures from a single linker node. The Boc-protected carboxylate, upon deprotection, yields a free carboxylic acid for amide coupling with amine-containing ligands, providing a third conjugation site through orthogonal chemistry. The branched topology with multiple PEG arms provides enhanced aqueous solubility and conformational flexibility, critical for accommodating the spatial requirements of productive ternary complex formation. Researchers employ this linker to explore multivalent degrader designs and to investigate how branched architectures with multiple click-chemistry handles influence degradation potency, selectivity, and the modularity of PROTAC assembly in targeted protein degradation studies.

N-(PEG2-Boc)-N-bis(PEG2-propargyl)

Structure of 2100306-69-0

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Category
PROTAC Linker
Molecular Formula
C₂₅H₄₃NO₈
Molecular Weight
485.61

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

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Purity
98%
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
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Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl 3-[2-[2-[bis[2-(2-prop-2-ynoxyethoxy)ethyl]amino]ethoxy]ethoxy]propanoate
Synonyms
N-(t-butyl ester-PEG2)-N-bis(PEG2-propargyl)
InChI Key
SNTDJGZACCWQRM-UHFFFAOYSA-N
InChI
InChI=1S/C25H43NO8/c1-6-12-28-18-21-31-15-9-26(10-16-32-22-19-29-13-7-2)11-17-33-23-20-30-14-8-24(27)34-25(3,4)5/h1-2H,8-23H2,3-5H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCN(CCOCCOCC#C)CCOCCOCC#C

This branched linker presents terminal alkynes together with an acid-labile protected carboxyl arm around a tertiary amine center. It is suited to convergent, click-enabled or multivalent PROTAC construction, while the masked acid supports a later orthogonal coupling step. Detailed characteristics follow.

Structure: A tertiary amine connects oligoether arms bearing propargyl ether termini and a tert-butyl propanoate arm. The scaffold contains terminal carbon–carbon triple bonds, numerous ether linkages, a basic tertiary amine, and an ester carbonyl, producing a flexible branched architecture.

Reactivity: Each terminal alkyne can react with an azide through cuprous-catalyzed cycloaddition in a water-compatible solvent with a copper-stabilizing ligand and reductant. Stoichiometry governs whether partial or extensive click substitution occurs. Acidic cleavage of the tert-butyl ester subsequently reveals a carboxyl group for activated amidation, although copper-binding by the tertiary amine may require catalyst optimization and metal-removal workup.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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