Boc-PEG5-methyl ester

 CAS No.: 1807530-04-6  Cat No.: BP-500957 4.5  

Boc-PEG5-methyl ester is a heterobifunctional PEG linker featuring a Boc-protected carboxylate at one terminus and a methyl ester at the other, connected through a pentaethylene glycol spacer. The Boc group provides acid-labile protection for the proximal carboxylic acid, while the methyl ester serves as an orthogonal, base-labile protecting group for the distal carboxylate. This differentially protected architecture enables sequential deprotection and conjugation strategies: the Boc group can be removed under mild acidic conditions to reveal a free carboxylic acid for initial amide coupling with one amine-containing ligand, followed by selective hydrolysis of the methyl ester under basic conditions to liberate the second carboxylate for coupling with a different amine-containing ligand. The orthogonal stability of Boc and methyl ester groups ensures selective, stepwise functionalization without cross-reactivity. The extended PEG spacer enhances aqueous solubility and provides conformational flexibility necessary for bridging the spatial gap between the target protein-binding ligand and the E3 ubiquitin ligase-recruiting moiety in PROTAC constructs. Researchers employ this linker for sequential PROTAC assembly, investigating how extended PEG spacers influence degradation potency and reproducibility in targeted protein degradation research.

Boc-PEG5-methyl ester

Structure of 1807530-04-6

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PROTAC Linker
Molecular Formula
C₁₉H₃₆O₉
Molecular Weight
408.48

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

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IUPACName
methyl 3-[2-[2-[2-[2-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
InChI Key
BJNQNORQYFJOCD-UHFFFAOYSA-N
InChI
InChI=1S/C19H36O9/c1-19(2,3)28-18(21)6-8-24-10-12-26-14-16-27-15-13-25-11-9-23-7-5-17(20)22-4/h5-16H2,1-4H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCOCCOCCC(=O)OC

This flexible oligoether linker carries differentiated tert-butyl and methyl ester termini for sequential carboxyl unveiling. Their contrasting cleavage profiles facilitate directional attachment of amine-bearing ligands, making the spacer useful for modular, unsymmetrical PROTAC construction. Structural and reaction features follow.

Structure: A linear, ether-rich chain links tert-butyl and methyl propanoate groups. Its principal bonds include flexible carbon–oxygen and carbon–carbon single bonds plus ester carbonyls. The absence of free nucleophiles limits premature coupling, while the chemically differentiated termini enable staged activation.

Reactivity: Selective acidic cleavage can expose the tert-butyl-protected acid, whereas controlled ester hydrolysis can reveal the methyl-protected terminus. The resulting acid is suitable for carbodiimide-, phosphonium-, or uronium-mediated coupling with an amine in a dry polar aprotic solvent and base. Protecting-group order should be chosen after evaluating the acid and base tolerance of the recruited ligands.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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