Ald-Ph-PEG5-Boc

Name: Ald-Ph-PEG5-Boc
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 1433996-83-8

Cat No.: BP-500673 4.5

Ald-Ph-PEG5-Boc is a heterobifunctional PEG linker comprising a benzaldehyde moiety at one terminus and a Boc-protected carboxylate at the other, bridged by an extended pentaethylene glycol spacer. The aromatic aldehyde provides a chemoselective electrophilic handle that forms stable oxime or hydrazone linkages with aminooxy- or hydrazide-functionalized biomolecules under mild, metal-free aqueous conditions, making it compatible with sensitive protein ligands. The Boc group protects the distal carboxylic acid during conjugation and can be removed under standard acidic conditions to reveal a free carboxylate for subsequent amide bond formation. The extended PEG chain confers enhanced aqueous solubility and increased conformational flexibility, both critical for bridging the target protein-binding warhead and the E3 ubiquitin ligase-recruiting ligand across greater intermolecular distances within the ternary complex. In PROTAC design, linker length is a critical determinant of degradation efficiency, and this compound occupies an intermediate position within the homologous aldehyde-phenyl PEG series, enabling researchers to systematically probe the conformational space between constrained and high-entropy linkers to optimize ternary complex geometry and degradation potency.

Structure of 1433996-83-8

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Category

PROTAC Linker

Molecular Formula

C₂₂H₃₄O₈

Molecular Weight

426.50

* 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-[2-[2-[2-(4-formylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]propanoate

InChI Key

QVWIJQYADDDNJZ-UHFFFAOYSA-N

InChI

InChI=1S/C22H34O8/c1-22(2,3)30-21(24)8-9-25-10-11-26-12-13-27-14-15-28-16-17-29-20-6-4-19(18-23)5-7-20/h4-7,18H,8-17H2,1-3H3

SMILES

CC(C)(C)OC(=O)CCOCCOCCOCCOCCOC1=CC=C(C=C1)C=O

This heterobifunctional linker pairs an aromatic aldehyde with a protected carboxyl terminus across an extended oligoether spacer. It supports chemoselective ligand attachment and adjustable separation within PROTACs while retaining a handle for subsequent amidation. Detailed structural and reactive properties follow.

Structure: A para-formyl phenyl ether is connected to a longer, flexible oligoether chain terminating in tert-butyl propanoate. The linker contains aromatic bonds, multiple ether linkages, an aldehyde carbonyl, and an ester carbonyl, combining a rigid recognition-adjacent end with a mobile spacer.

Reactivity: The aromatic aldehyde undergoes aminooxy condensation to provide an oxime under mildly acidic aqueous-organic conditions, optionally with nucleophilic catalysis. The tert-butyl ester can be cleaved with acid in dichloromethane to reveal a carboxyl group. Subsequent activation with a carbodiimide, phosphonium, or uronium coupling reagent enables amide formation with an amine-bearing ligand in a polar aprotic solvent.

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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