N-Boc-N-bis(PEG3-NHS ester)

 CAS No.: 2055042-31-2  Cat No.: BP-501461 4.5  

N-Boc-N-bis(PEG3-NHS ester) is a bifunctional PEG-based linker bearing two terminal N-hydroxysuccinimide (NHS) ester groups on short PEG3 arms, with an N-Boc-protected central amine that provides controlled reactivity and improved handling stability. Structurally, it functions as a flexible, hydrophilic spacer that can be conjugated to two different biomolecular or ligand components through NHS ester–mediated amide bond formation with primary amines (for example, lysine residues on proteins or amine-terminated targeting ligands). In PROTAC and targeted protein degradation workflows, such linkers are used to tune the spatial relationship and effective reach between the “warhead” and the recruitment moiety, thereby influencing ternary complex formation and degradation efficiency. Its PEG3 architecture helps reduce nonspecific hydrophobic interactions and can enhance solubility of conjugates, facilitating reproducible synthesis and characterization of multi-component degraders for mechanistic and optimization studies.

N-Boc-N-bis(PEG3-NHS ester)

Structure of 2055042-31-2

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PROTAC Linker
Molecular Formula
C₃₁H₄₉N₃O₁₆
Molecular Weight
719.73

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

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IUPACName
(2,5-dioxopyrrolidin-1-yl) 3-[2-[2-[2-[2-[2-[2-[3-(2,5-dioxopyrrolidin-1-yl)oxy-3-oxopropoxy]ethoxy]ethoxy]ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethoxy]ethoxy]ethoxy]propanoate
InChI Key
PQSUBGGFVYSVNA-UHFFFAOYSA-N
InChI
InChI=1S/C31H49N3O16/c1-31(2,3)48-30(41)32(10-14-44-18-22-46-20-16-42-12-8-28(39)49-33-24(35)4-5-25(33)36)11-15-45-19-23-47-21-17-43-13-9-29(40)50-34-26(37)6-7-27(34)38/h4-23H2,1-3H3
SMILES
CC(C)(C)OC(=O)N(CCOCCOCCOCCC(=O)ON1C(=O)CCC1=O)CCOCCOCCOCCC(=O)ON2C(=O)CCC2=O

This PROTAC linker reagent, N-Boc-N-bis(PEG3-NHS ester), provides a versatile, bifunctional PEG-based platform for constructing targeted protein degraders. Its dual N-hydroxysuccinimide (NHS) ester termini enable efficient coupling to amine-bearing ligands, while the Boc-protected core supports controlled handling and subsequent functionalization. The PEG3 spacer promotes aqueous compatibility and can help tune linker flexibility in degradation constructs. Detailed structural and reactivity considerations are provided below to guide experimental PROTAC synthesis.

Structure: The molecule contains a Boc-protected nitrogen center and two PEG3 chains terminating in NHS ester groups. The NHS esters are activated carbonate-like acylating functionalities, supported by ether linkages within the PEG segments. Overall, it is an amphiphilic, water-compatible linker designed for bioconjugation chemistry.

Reactivity: Suitable coupling typically proceeds via nucleophilic acyl substitution of NHS esters by primary amines on target-binding ligands under mildly basic conditions. Use anhydrous or low-water compatible solvents such as dimethylformamide or dimethyl sulfoxide, or buffered aqueous media when compatible with the NHS ester lifetime. No special catalysts are generally required; the reaction is driven by amine nucleophilicity and controlled pH, followed by purification to remove hydrolyzed NHS byproducts.

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

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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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