Ald-Ph-PEG2-Boc

Name: Ald-Ph-PEG2-Boc
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 2100306-65-6

Cat No.: BP-500608 4.5

Ald-Ph-PEG2-Boc is a heterobifunctional polyethylene glycol linker featuring an aromatic aldehyde moiety at one terminus and a Boc-protected carboxyl group at the other, connected through a short PEG spacer. The benzaldehyde group provides a reactive electrophilic handle for chemoselective bioconjugation, enabling formation of stable imine or oxime linkages with aminooxy- or hydrazide-functionalized ligands under mild aqueous conditions. The Boc group serves as an acid-labile protecting group for the terminal carboxylic acid, which can be deprotected to reveal a free carboxylate for subsequent amide coupling with amine-containing warheads or E3 ligase ligands. In PROTAC design, this linker facilitates the covalent assembly of bifunctional degrader molecules by bridging the target protein-binding ligand and the E3 ubiquitin ligase-recruiting moiety through a defined, moderately flexible PEG tether. The incorporated aromatic ring introduces conformational rigidity that may contribute to favorable protein-protein interactions within the ternary complex. Researchers utilize this linker to systematically investigate how aromatic rigidity and PEG flexibility collectively modulate degradation efficiency in targeted protein degradation studies.

Structure of 2100306-65-6

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PROTAC Linker

Molecular Formula

C₁₆H₂₂O₅

Molecular Weight

294.34

* 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

tert-butyl 3-[2-(4-formylphenoxy)ethoxy]propanoate

InChI Key

HIKDMVVPLDWKAB-UHFFFAOYSA-N

InChI

InChI=1S/C16H22O5/c1-16(2,3)21-15(18)8-9-19-10-11-20-14-6-4-13(12-17)5-7-14/h4-7,12H,8-11H2,1-3H3

SMILES

CC(C)(C)OC(=O)CCOCCOC1=CC=C(C=C1)C=O

This heterobifunctional linker combines an aromatic aldehyde for chemoselective conjugation with an acid-labile protected carboxyl terminus. Its flexible oligoether segment can provide spatial separation between recruited ligands in PROTAC assembly. The molecular structure and practical reactivity are described in detail below.

Structure: The molecule contains a para-substituted phenyl ring bearing an aldehyde, an aryl ether, a flexible oligoether chain, and a terminal tert-butyl propanoate. Covalent features include aromatic carbon bonds, ether linkages, an aldehyde carbonyl, and a protected ester carbonyl.

Reactivity: The aldehyde can condense with an aminooxy-functionalized ligand to form an oxime under mildly acidic aqueous-organic conditions; aniline derivatives may accelerate this process. Alternatively, acid treatment in dichloromethane can cleave the tert-butyl ester, after which the liberated carboxyl group may be activated with a carbodiimide or uronium reagent and coupled to an amine under basic, anhydrous conditions.

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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