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

 CAS No.: 2100306-86-1  Cat No.: BP-500222  Purity: 98% 4.5  

N-Boc-N-bis(PEG2-propargyl) is a protected, bis-functional polyethylene glycol (PEG) linker bearing two terminal propargyl groups and a Boc-protected nitrogen, providing a short, flexible hydrophilic spacer with two orthogonal handles for conjugation. In PROTAC construction, this scaffold is used to connect or spatially separate the two recognition modules (a ligand for an E3 ligase and a ligand for the target protein) by installing propargyl “click” sites that can be coupled to complementary azide-bearing partners via copper-catalyzed azide–alkyne cycloaddition. The PEG segments enhance aqueous solubility and can reduce steric interference, while the bis-propargyl architecture enables multivalent or symmetric linker geometries that may improve ternary complex formation. As a practical building block, it supports systematic linker optimization by allowing researchers to tune distance, flexibility, and conjugation stoichiometry in targeted protein degradation studies.

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

Structure of 2100306-86-1

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Category
PROTAC Linker
Molecular Formula
C₁₉H₃₁NO₆
Molecular Weight
369.45

* 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 N,N-bis[2-(2-prop-2-ynoxyethoxy)ethyl]carbamate
Synonyms
tert-butyl bis(2-(2-(prop-2-yn-1-yloxy)ethoxy)ethyl)carbamate; tert-butyl N,N-bis({2-[2-(prop-2-yn-1-yloxy)ethoxy]ethyl})carbamate; 4,7,13,16-Tetraoxa-10-azanonadeca-1,18-diynoic acid, 1,1-dimethylethyl ester
InChI Key
NSGYNRBYZCGGOL-UHFFFAOYSA-N
InChI
InChI=1S/C19H31NO6/c1-6-10-22-14-16-24-12-8-20(18(21)26-19(3,4)5)9-13-25-17-15-23-11-7-2/h1-2H,8-17H2,3-5H3
SMILES
CC(C)(C)OC(=O)N(CCOCCOCC#C)CCOCCOCC#C

N-Boc-N-bis(PEG2-propargyl), is designed to provide a protected, bifunctional scaffold that enables efficient conjugation of two targeting components through orthogonal click-compatible handles. Its PEG-containing segments support solubility and conformational flexibility, while the propargyl termini facilitate copper-catalyzed azide–alkyne cycloaddition for modular assembly. The Boc-protection strategy helps maintain controlled reactivity during synthesis, and the molecule will be described in detail below.

Structure: The linker contains a Boc-protected nitrogen center connected to two PEG2-terminated propargyl arms. It features ether linkages within the PEG segments, carbamate functionality from the Boc group, and terminal carbon–carbon triple bonds suitable for click chemistry. These elements collectively increase hydrophilicity and provide flexible spacing.

Reactivity: The propargyl groups participate in copper-catalyzed azide–alkyne cycloaddition, enabling rapid formation of stable triazole linkages under mild conditions. Typical approaches use Cu(I) generated in situ from copper salts with a reducing agent, in polar organic or mixed solvent systems compatible with biomolecule conjugation. The Boc group can be retained during coupling steps and removed under standard acid-mediated deprotection when subsequent amide or amine functionalization is required.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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