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904821 Sigma-Aldrich

(S,R,S)-AHPC-C6-PEG3-butyl azide

≥95%

Synonym: (2S,4R)-1-((S)-22-Azido-2-(tert-butyl)-4-oxo-10,13,16-trioxa-3-azadocosanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide, AHPC-6-2-2-6-N3, Crosslinker−E3 Ligase ligand conjugate, Protein degrader building block for PROTAC® research, Template for synthesis of targeted protein degrader, VH032 conjugate

  • CAS Number 2300155-90-0

  • Empirical Formula (Hill Notation) C38H59N7O7S

  • Molecular Weight 757.98

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Properties

Related Categories Chemical Biology, Chemical Synthesis, Degrader Building Blocks, Degrader Building Blocks for Click Chemistry
assay   ≥95%
form   powder or crystals
reaction suitability   reaction type: click chemistry
storage temp.   2-8°C

Description

Application

Protein degrader builiding block (S,R,S)-AHPC-C6-PEG3-butyl azide enables the synthesis of molecules for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. This conjugate contains a von Hippel-Lindau (VHL)-recruiting ligand, a linker with both hydrophobic and hydrophilic moieties, and a pendant azide for click chemistry with a target ligand. Because even slight alterations in ligands and crosslinkers can affect ternary complex formation between the target, E3 ligase, and PROTAC, many analogs are prepared to screen for optimal target degradation. When used with other protein degrader building blocks with a pendant azide group, parallel synthesis can be used to more quickly generate PROTAC libraries that feature variation in crosslinker length, composition, and E3 ligase ligand.

Other Notes

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Portal: Building PROTAC® Degraders for Targeted Protein Degradation

Targeted Protein Degradation by Small Molecules

Small-Molecule PROTACS: New Approaches to Protein Degradation

Targeted Protein Degradation: from Chemical Biology to Drug Discovery

Impact of linker length on the activity of PROTACs

Legal Information

PROTAC is a registered trademark of Arvinas Operations, Inc., and is used under license

Safety & Documentation

Safety Information

WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Degrader Building Blocks for Targeted Protein Degradation

An emerging strategy in drug discovery to access difficult-to-treat diseases is targeted protein degradation. While traditional small-molecule or antibody drugs may only allow access to ~20% of the p...
Keywords: Bacterial conjugations, Building blocks, Degradations, Diseases, Drug discovery, Ligands, Parallel synthesis

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