Amino-PEG10-t-butyl ester

 CAS No.: 1818294-42-6  Cat No.: BP-501090  Purity: >97% 4.5  

Amino-PEG10-t-butyl ester is a bifunctional polyethylene glycol (PEG) linker featuring a terminal primary amine and a protected carboxyl group masked as a tert-butyl ester. Structurally, it provides a flexible, hydrophilic chain of approximately ten ethylene glycol units that can project reactive groups away from bulky ligands, improving effective conjugation geometry and reducing steric interference. In PROTAC and targeted protein degradation workflows, the amine handle enables coupling to electrophilic warheads or E3-ligase–binding moieties through amide-forming or other standard bioconjugation chemistries, while the tert-butyl ester can be used as a protected carboxyl equivalent for subsequent activation/deprotection steps to generate an acid for controlled linkage formation. This linker value lies in its ability to tune linker length and polarity, often enhancing soluble behavior and supporting efficient formation of heterobifunctional degraders for systematic structure–activity studies.

Amino-PEG10-t-butyl ester

Structure of 1818294-42-6

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Category
PROTAC Linker
Molecular Formula
C27H55NO12
Molecular Weight
585.73
Appearance
Pale Yellow or Colorless Oily Matter

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

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Purity
>97%
Appearance
Pale Yellow or Colorless Oily Matter
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-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
Amino-PEG10-COOtBu; 3-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid tert-butyl ester; 2-Methyl-2-propanyl 1-amino-3,6,9,12,15,18,21,24,27,30-decaoxatritriacontan-33-oate; 3,6,9,12,15,18,21,24,27,30-Decaoxatritriacontan-33-oic acid, 1-amino-, 1,1-dimethylethyl ester; H2N-PEG10-CH2CH2COOtBu; Amino-PEG10-Boc
Boiling Point
606.9±50.0°C at 760 mmHg
Density
1.1±0.1 g/cm3
InChI Key
CXGGTGCHTQMBOC-UHFFFAOYSA-N
InChI
InChI=1S/C27H55NO12/c1-27(2,3)40-26(29)4-6-30-8-10-32-12-14-34-16-18-36-20-22-38-24-25-39-23-21-37-19-17-35-15-13-33-11-9-31-7-5-28/h4-25,28H2,1-3H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCN
1. Efficient Fmoc-Protected Amino Ester Hydrolysis Using Green Calcium(II) Iodide as a Protective Agent
Renaud Binette, Michael Desgagné, Camille Theaud, Pierre-Luc Boudreault Molecules. 2022 Apr 27;27(9):2788.doi: 10.3390/molecules27092788.
In order to modify amino acids, the C-terminus carboxylic acid usually needs to be protected, typically as a methyl ester. However, standard cleavage of methyl esters requires either highly basic or acidic conditions, which are not compatible with Fmoc or acid-labile protecting groups. This highlights the need for orthogonal conditions that permit selective deprotection of esters to create SPPS-ready amino acids. Herein, mild orthogonal ester hydrolysis conditions are systematically explored using calcium(II) iodide as a protective agent for the Fmoc protecting group and optimized for a broad scope of amino esters. Our optimized reaction improved on the already known trimethyltin hydroxide, as it produced better yields with greener, inexpensive chemicals and a less extensive energy expenditure.

This Amino-PEG10-t-butyl ester linker is designed to serve as a versatile polyethylene glycol (PEG)-based spacer bearing an amino functionality and a protected carboxyl group. Its hydrophilic PEG character supports solubility and favorable linker flexibility in targeted protein degradation constructs, while the t-butyl ester enables controlled downstream conjugation. The molecule is well suited for assembling PROTACs where modular attachment of ligands and controlled handling of functional groups are required; detailed structural and reactivity considerations are provided below.

Structure: The linker comprises a PEG oligomer segment connected to an amino group and a carboxyl function masked as a t-butyl ester. It contains ether linkages along the PEG chain, an amine for coupling, and an ester carbonyl that is stable under mild conditions yet removable under acidic cleavage.

Reactivity: For PROTAC assembly, the amino group can be used for amide or urea bond formation via standard coupling chemistries, typically employing activated carboxylic acid derivatives. The t-butyl ester can be deprotected under acidic conditions to reveal a carboxylic acid for subsequent conjugation. Common approaches use peptide-coupling reagents and compatible solvents such as polar aprotic media, with reaction monitoring to ensure selective deprotection and minimize side reactions.

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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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