N-Boc-N-bis(PEG3-acid)

 CAS No.: 2055023-35-1  Cat No.: BP-500854 4.5  

N-Boc-N-bis(PEG3-acid) is a protected, bis-functional polyethylene glycol linker bearing two PEG3 carboxylic acid termini and a Boc-protected nitrogen, providing a convenient scaffold for constructing PROTACs and related targeted protein degradation conjugates. Structurally, it combines a central amide-forming handle with two short, hydrophilic PEG arms that can be activated and coupled to complementary ligands (e.g., E3 ligase recruiters or target-binding moieties) through amide-bond formation. The PEG3 segments act as flexible spacers that can improve solubility, reduce nonspecific hydrophobic interactions, and help tune the effective distance and relative orientation between the two binding components, thereby supporting efficient ternary complex formation. In targeted degradation research, this linker is valuable for systematically varying linker length and polarity while maintaining a defined conjugation chemistry, facilitating optimization of potency, selectivity, and cellular performance in PROTAC development workflows.

N-Boc-N-bis(PEG3-acid)

Structure of 2055023-35-1

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PROTAC Linker
Molecular Formula
C₂₃H₄₃NO₁₂
Molecular Weight
525.59

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

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IUPACName
3-[2-[2-[2-[2-[2-[2-(2-carboxyethoxy)ethoxy]ethoxy]ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethoxy]ethoxy]ethoxy]propanoic acid
InChI Key
HVRLCVIGYIBUGD-UHFFFAOYSA-N
InChI
InChI=1S/C23H43NO12/c1-23(2,3)36-22(29)24(6-10-32-14-18-34-16-12-30-8-4-20(25)26)7-11-33-15-19-35-17-13-31-9-5-21(27)28/h4-19H2,1-3H3,(H,25,26)(H,27,28)
SMILES
CC(C)(C)OC(=O)N(CCOCCOCCOCCC(=O)O)CCOCCOCCOCCC(=O)O

N-Boc-N-bis(PEG3-acid) is a polyethylene glycol (PEG)-based PROTAC linker building block designed to provide aqueous compatibility, conformational flexibility, and a reliable handle for bioconjugation chemistry. Its PEG3-derived segments can help tune linker solubility and spatial presentation between the target-binding and E3-recruiting components. The Boc-protected amine functionality supports controlled coupling strategies, while the terminal acid groups enable robust attachment to amide-forming partners. Detailed structural and reactivity considerations for PROTAC assembly are provided below.

Structure: The linker contains a Boc-protected nitrogen center connected to PEG3 chains, featuring ether-rich segments that confer hydrophilicity and flexibility. It includes carboxylic acid functionality suitable for activation and subsequent amide bond formation, along with carbamate character from the Boc protecting group.

Reactivity: For PROTAC construction, the carboxylic acids are typically converted to activated esters or activated carboxylates using standard coupling reagents under mild base and controlled temperature. Amide bond formation proceeds via nucleophilic acyl substitution with amine-bearing ligands or linker fragments. The Boc group is generally retained during acid activation steps and can be removed under appropriate acidic conditions when deprotection is required for downstream coupling. Common solvents include polar aprotic media compatible with coupling chemistry.

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