Propargyl-PEG3-NHBoc

 CAS No.: 1333880-60-6  Cat No.: BP-501052  Purity: ≥95% 4.5  

Propargyl-PEG3-NHBoc is a heterobifunctional, PEG-based linker featuring a terminal propargyl (alkyne) handle and a protected amine (Boc) at the other end, connected through a short, flexible three-unit poly(ethylene glycol) chain. Structurally, its PEG segment provides aqueous solubility and conformational mobility, while the alkyne enables bioorthogonal conjugation strategies such as copper-catalyzed azide–alkyne cycloaddition or related click chemistries used to attach the linker to azide-functionalized ligands or payloads. The Boc-protected amine serves as a masked reactive site for subsequent deprotection and coupling, allowing controlled formation of amide or carbamate bonds during PROTAC assembly. In targeted protein degradation workflows, this linker is valuable for modular synthesis, enabling researchers to tune spatial separation and attachment geometry between a recruiting ligand and an E3 ligase binder, which can strongly influence ternary complex formation and degradation potency.

Propargyl-PEG3-NHBoc

Structure of 1333880-60-6

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Category
PROTAC Linker
Molecular Formula
C14H25NO5
Molecular Weight
287.36
Related CAS
1520979-34-3 (polymer)

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

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Purity
≥95%
Solubility
Soluble in DCM, DMF, DMSO
Storage
Store at -20°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl N-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethyl]carbamate
Synonyms
t-Boc-N-Amido-PEG3-propargyl; Boc-NH-PEG3-propargyl; Boc-N-Amido-PEG3-Alkyne; tert-butyl (2-(2-(2-(prop-2-yn-1-yloxy)ethoxy)ethoxy)ethyl)carbamate; 5,8,11-Trioxa-2-azatetradec-13-ynoic acid, 1,1-dimethylethyl ester; tert-butyl N-(2-{2-[2-(prop-2-yn-1-yloxy)ethoxy]ethoxy}ethyl)carbamate; 2-Methyl-2-propanyl (2-{2-[2-(2-propyn-1-yloxy)ethoxy]ethoxy}ethyl)carbamate; Carbamic acid, N-[2-[2-[2-(2-propyn-1-yloxy)ethoxy]ethoxy]ethyl]-, 1,1-dimethylethyl ester
Boiling Point
386.4±32.0°C (Predicted)
Density
1.045±0.06 g/cm3 (Predicted)
InChI Key
IKRULGOPBBCYPJ-UHFFFAOYSA-N
InChI
InChI=1S/C14H25NO5/c1-5-7-17-9-11-19-12-10-18-8-6-15-13(16)20-14(2,3)4/h1H,6-12H2,2-4H3,(H,15,16)
SMILES
CC(C)(C)OC(=O)NCCOCCOCCOCC#C

Propargyl-PEG3-NHBoc is a PEG-based PROTAC linker building block designed to connect ligands while providing hydrophilic spacing and a functional handle for controlled conjugation. Its propargyl group enables orthogonal “click” chemistry for efficient assembly, while the protected amine supports later deprotection and coupling strategies. These features make it well suited for constructing targeted protein degradation (PROTAC) molecules, where linker length, polarity, and modular reactivity strongly influence productive ternary complex formation. Detailed structural and reactivity considerations are provided below.

Structure: The linker comprises a propargyl-terminated polyethylene glycol chain bearing an N-Boc-protected amine. It contains an alkyne for bioorthogonal conjugation, ether linkages within the PEG segment for conformational flexibility, and a Boc carbamate that stabilizes the amine during synthetic steps.

Reactivity: PROTAC assembly commonly uses the terminal alkyne in copper-catalyzed azide–alkyne cycloaddition to form stable triazole linkages with azide-bearing partners. Typical conditions employ a Cu(I) source, an appropriate ligand to control copper speciation, and polar solvents compatible with PEG solubility. The Boc group can be removed under standard acid-mediated deprotection to reveal the amine for subsequent amide or urea coupling, enabling modular ligand attachment.

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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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