Azido-PEG8-t-butyl ester

 CAS No.: 1623791-99-0  Cat No.: BP-501084  Purity: ≥95% 4.5  

Azido-PEG8-t-butyl ester is a heterobifunctional polyethylene glycol (PEG) linker bearing a terminal azide for bioorthogonal conjugation and a protected carboxyl group as a tert-butyl ester. Structurally, it consists of an eight-unit PEG chain that provides aqueous solubility, conformational flexibility, and a defined spatial spacer between the two reactive handles. In PROTAC design, the azide enables efficient attachment to alkyne-containing ligands or handles via copper-free click chemistry, allowing researchers to install the linker onto one component while the ester functionality can be used for subsequent coupling strategies or deprotection to reveal a carboxyl group for amide/ester bond formation. The PEG backbone helps reduce steric interference and can improve the effective proximity and productive orientation required for ternary complex formation. This linker is therefore valuable for constructing modular PROTACs and related targeted degradation probes with controlled linker length and robust, chemoselective conjugation workflows.

Azido-PEG8-t-butyl ester

Structure of 1623791-99-0

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Category
PROTAC Linker
Molecular Formula
C23H45N3O10
Molecular Weight
523.62
Appearance
Colorless Liquid

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

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Purity
≥95%
Solubility
Soluble in DCM, DMF, DMSO, Water
Appearance
Colorless Liquid
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl 3-[2-[2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
Azido-PEG8-Boc; 4,7,10,13,16,19,22,25-Octaoxaheptacosanoic acid, 27-azido-, 1,1-dimethylethyl ester; N3-PEG8-CH2CH2COOtBu; 2-Methyl-2-propanyl 1-azido-3,6,9,12,15,18,21,24-octaoxaheptacosan-27-oate; 3,6,9,12,15,18,21,24-Octaoxaheptacosan-27-oic acid, 1-azido-, 1,1-dimethylethyl ester
InChI Key
LBNCLZBCQUTBAP-UHFFFAOYSA-N
InChI
InChI=1S/C23H45N3O10/c1-23(2,3)36-22(27)4-6-28-8-10-30-12-14-32-16-18-34-20-21-35-19-17-33-15-13-31-11-9-29-7-5-25-26-24/h4-21H2,1-3H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCOCCOCCOCCOCCOCCN=[N+]=[N-]
ConcentrationVolumeMass1 mg5 mg10 mg
1 mM1.9098 mL9.5489 mL19.0978 mL
5 mM0.3820 mL1.9098 mL3.8196 mL
10 mM0.1910 mL0.9549 mL1.9098 mL

Azido-PEG8-t-butyl ester is a PEG-based, azide-functional linker designed for modular assembly of PROTACs and other targeted degradation constructs. Its flexible polyether scaffold supports favorable linker conformations, while the terminal azide enables bioorthogonal conjugation strategies. The tert-butyl ester provides a protected carboxyl functionality that can be unmasked under controlled conditions, facilitating subsequent coupling to ligands. The points below describe its structure and practical reactivity considerations in PROTAC workflows.

Structure: This linker features a poly(ethylene glycol) chain that imparts conformational flexibility and hydrophilicity. A terminal azide group serves as a versatile chemical handle for click-type conjugation. The carboxyl functionality is masked as a tert-butyl ester, providing acid-labile protection while maintaining chemical stability during synthesis.

Reactivity: The azide group is compatible with copper(I)-catalyzed azide–alkyne cycloaddition or strain-promoted azide–alkyne cycloaddition, enabling efficient attachment of complementary alkyne-bearing ligands under standard click-chemistry conditions. The tert-butyl ester is typically deprotected using mild acid to reveal the carboxyl for further amide or related coupling reactions. Selection of solvent systems and coupling reagents should follow established ester-to-acid and carboxyl-derivatization protocols used in PROTAC linker synthesis.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
g/mol
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