N-(Azido-PEG2)-N-bis(PEG4-Boc)

 CAS No.: 2112731-81-2  Cat No.: BP-500786  Purity: 98% 4.5  

N-(Azido-PEG2)-N-bis(PEG4-Boc) is a branched polyethylene glycol linker featuring a central tertiary amine bearing three functional arms: an azide-terminated short PEG chain and two extended Boc-protected carboxylate arms. This trifunctional architecture enables sophisticated, orthogonal conjugation strategies in PROTAC assembly. The azide group provides a bioorthogonal handle for copper-catalyzed or strain-promoted azide-alkyne cycloaddition, allowing selective coupling to alkyne-functionalized ligands. The two Boc-protected carboxylates, upon deprotection, yield free carboxylic acids that can be conjugated to amine-containing warheads or E3 ubiquitin ligase-recruiting moieties via standard amide coupling chemistry. The branched topology is particularly valuable for constructing multivalent PROTACs, where two identical or distinct ligands can be appended alongside an azide-functionalized moiety to a single linker scaffold. The extended PEG arms provide enhanced aqueous solubility and conformational flexibility critical for bridging the spatial requirements of productive ternary complex formation. Researchers employ this linker to explore branched, trivalent degrader architectures and to investigate how multivalent ligand presentation and modular assembly strategies influence degradation potency, selectivity, and the overall physicochemical properties of PROTAC molecules in targeted protein degradation studies.

N-(Azido-PEG2)-N-bis(PEG4-Boc)

Structure of 2112731-81-2

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Category
PROTAC Linker
Molecular Formula
C₃₆H₇₀N₄O₁₄
Molecular Weight
782.96

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

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Purity
98%
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-[2-[2-[2-(2-azidoethoxy)ethoxy]ethyl-[2-[2-[2-[2-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]ethoxy]ethoxy]ethoxy]ethyl]amino]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
N-(Azido-PEG2)-N-bis(PEG4-t-butyl ester)
InChI Key
QMUHVUPHHRSFNU-UHFFFAOYSA-N
InChI
InChI=1S/C36H70N4O14/c1-35(2,3)53-33(41)7-13-43-19-25-49-29-31-51-27-23-47-17-11-40(10-16-46-22-21-45-15-9-38-39-37)12-18-48-24-28-52-32-30-50-26-20-44-14-8-34(42)54-36(4,5)6/h7-32H2,1-6H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCOCCN(CCOCCOCCN=[N+]=[N-])CCOCCOCCOCCOCCC(=O)OC(C)(C)C

This branched linker combines an azido oligoether arm with protected carboxyl-bearing arms around a tertiary amine center. It supports click-based anchoring followed by multichannel amidation, enabling systematic exploration of branched or multivalent PROTAC geometries. Structural and reactive features are detailed below.

Structure: A tertiary amine branch point carries an azido-terminated oligoether substituent and extended ether-rich arms ending as tert-butyl propanoates. The structure contains flexible ether and carbon–nitrogen bonds, basic tertiary amine character, ester carbonyls, and a terminal azide.

Reactivity: The azide undergoes cuprous-catalyzed cycloaddition with terminal alkynes in aqueous-organic or polar organic media, normally with a copper ligand and reductant. Subsequent acidic treatment reveals carboxyl groups from the tert-butyl esters without requiring modification of the triazole product. Activated amidation can then install amine-bearing ligands; careful stoichiometry or selective protection is needed to control substitution across the branched acid termini.

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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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