Acid-C1-PEG5-Boc

Name: Acid-C1-PEG5-Boc
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 2304558-22-1

Cat No.: BP-500798 4.5

Acid-C1-PEG5-Boc is a heterobifunctional PEG linker featuring a free carboxylic acid at one terminus and a Boc-protected carboxylate at the other, connected through an extended pentaethylene glycol spacer. The unprotected carboxylic acid provides an immediately available reactive handle for direct amide coupling with primary amine-containing ligands, such as target protein warheads or E3 ubiquitin ligase-recruiting moieties, using standard carbodiimide activation chemistry. The Boc group protects the distal carboxylate during the initial conjugation step and can be selectively removed under mild acidic conditions to reveal a second free carboxylic acid for subsequent amide coupling with a different amine-containing ligand. This orthogonally protected, heterobifunctional design enables sequential and chemoselective installation of two distinct ligands without the need for additional protecting group manipulations. The extended PEG chain confers enhanced aqueous solubility and substantial conformational flexibility, both of which are critical for accommodating the intermolecular distances required for productive ternary complex formation between the target protein and the E3 ubiquitin ligase. Researchers utilize this linker to systematically investigate how extended PEG spacer lengths influence degradation efficiency and selectivity in targeted protein degradation studies.

Structure of 2304558-22-1

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PROTAC Linker

Molecular Formula

C₁₇H₃₂O₉

Molecular Weight

380.43

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

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Please store the product under the recommended conditions in the Certificate of Analysis.

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IUPACName

2-[2-[2-[2-[2-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetic acid

InChI Key

HEXUSUWJDURSOW-UHFFFAOYSA-N

InChI

InChI=1S/C17H32O9/c1-17(2,3)26-16(20)4-5-21-6-7-22-8-9-23-10-11-24-12-13-25-14-15(18)19/h4-14H2,1-3H3,(H,18,19)

SMILES

CC(C)(C)OC(=O)CCOCCOCCOCCOCCOCC(=O)O

This differentially protected oligoether linker contains a free carboxylic acid and an acid-labile ester at opposite ends. It permits directional, sequential coupling of amine-bearing ligands and offers a flexible polar spacer for assembling unsymmetrical PROTACs. Its chemical features and use are described below.

Structure: The molecule is an ether-rich linear chain bounded by a free acetic acid and a tert-butyl propanoate. It contains carboxylic acid and ester carbonyls, multiple flexible ether bonds, and no free amine; the differentiated termini support sequential synthetic manipulation.

Reactivity: Activate the free acid with a carbodiimide, phosphonium, or uronium reagent and couple it to an amine under mildly basic, anhydrous conditions in dimethylformamide or a similar solvent. The tert-butyl ester remains available for later acid-mediated cleavage. After deprotection, the newly exposed acid can undergo a further amidation, enabling directional assembly while minimizing statistical mixtures.

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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