t-Butoxycarbonyl-PEG4-NHS ester

 CAS No.: 1835759-75-5  Cat No.: BP-501026 4.5  

t-Butoxycarbonyl-PEG4-NHS ester is a PEG-based, amine-reactive linker designed for PROTAC and targeted protein degradation workflows. Structurally, it combines a terminal N-hydroxysuccinimide (NHS) ester for efficient conjugation to primary amines on ligands (e.g., lysine-bearing peptides or engineered small-molecule handles), with a PEG4 spacer that provides aqueous solubility, conformational flexibility, and reduced steric interference between the two PROTAC components. The Boc protecting group on the other functional end enables controlled downstream deprotection, allowing sequential assembly strategies when orthogonal functionalization is required. In PROTAC design, this linker mediates stable covalent attachment between the targeting moiety and the E3 ligase ligand, while the PEG segment helps maintain productive geometry for ternary complex formation and can improve handling and formulation for in vitro assays. This reagent is valuable for building modular, tunable conjugates that support systematic linker optimization in targeted degradation research.

t-Butoxycarbonyl-PEG4-NHS ester

Structure of 1835759-75-5

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PROTAC Linker
Molecular Formula
C₂₀H₃₃NO₁₀
Molecular Weight
447.48
Appearance
Liquid

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

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Appearance
Liquid
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 3-[2-[2-[2-[3-(2,5-dioxopyrrolidin-1-yl)oxy-3-oxopropoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
t-Butoxycarbonyl-PEG4-NHS ester; 1835759-75-5; Boc-PEG4-C2-NHS ester; OtBu-PEG4-SPA; T-BUTOXYCARBONYL-PEG4-NHSESTER; 1-tert-butyl 2,5-dioxopyrrolidin-1-yl 4,7,10,13-tetraoxahexadecanedioate; AKOS040743111; BP-22936
InChI Key
QYNINGPFVBXEGJ-UHFFFAOYSA-N
InChI
InChI=1S/C20H33NO10/c1-20(2,3)30-18(24)6-8-26-10-12-28-14-15-29-13-11-27-9-7-19(25)31-21-16(22)4-5-17(21)23/h4-15H2,1-3H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCOCCC(=O)ON1C(=O)CCC1=O

This activated heterobifunctional oligoether linker combines an amine-reactive succinimidyl ester with an acid-labile protected carboxyl terminus. It supports direct, efficient amidation followed by carboxyl unveiling, providing a flexible route to sequential PROTAC ligand conjugation. Its key features follow.

Structure: An oligoether chain connects a tert-butyl propanoate to a terminal succinimidyl ester. The molecule contains flexible ether bonds, ester carbonyls, and a cyclic imide; the activated ester is electrophilic, whereas the tert-butyl ester masks the opposing carboxyl group.

Reactivity: React the succinimidyl ester with a primary or secondary amine in a dry polar solvent or mildly basic aqueous-organic medium; nucleophilic acyl substitution forms an amide and releases hydroxysuccinimide. Limit water exposure because hydrolysis competes with aminolysis. Subsequent acidic cleavage of the tert-butyl ester reveals a carboxyl group for another activated amidation, provided the installed ligand tolerates the deprotection conditions.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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Historical Records: 5-(Biotinamido)pentylazide | Biotin disulfide N-hydroxysuccinimide ester | Alkyne-PEG4-maleimide | Bis-(N,N'-amine-PEG3)-Cy5 | N-Boc-N-bis(PEG2-propargyl) | Fmoc-NH-PEG4-t-butyl ester | Boc-aminooxy-PEG4-propargyl | (+)-JQ1 carboxylic acid | β-Estradiol-6-one 6-(O-carboxymethyloxime) | N-(Boc-PEG1)-N-bis(PEG2-propargyl) | t-Butoxycarbonyl-PEG4-NHS ester

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