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917052 Sigma-Aldrich

(S,R,S)-AHPC-C3-NH2 hydrochloride

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≥95%

Synonym: (2S,4R)-1-((S)-2-(4-aminobutanamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride, Crosslinker−E3 Ligase ligand conjugate, Protein degrader building block for PROTAC® research, Template for synthesis of targeted protein degrader, VH032 conjugate

  • Empirical Formula (Hill Notation) C26H37N5O4S · xHCl

  • Molecular Weight 515.67 (free base basis)

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Properties

Quality Level   100
assay   ≥95%
form   powder or crystals
storage temp.   2-8°C

Description

Application

Protein degrader building block (S,R,S)-AHPC-C3-NH2 hydrochloride 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 and an alkyl-chain crosslinker with pendant amine for reactivity with an acid on the target warhead. Because even slight alterations in ligands, warheads, 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 terminal amine, 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

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
Peer-Reviewed Papers
15

References

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901488 (S,R,S)-AHPC-PEG2-NH2 hydrochloride, ≥95%
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911690 C5 Lenalidomide, ≥95%
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911658 Pomalidomide-C3-NH2 hydrochloride, ≥95%
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911712 C5 Lenalidomine-C6-NH2 hydrochloride, ≥95%
911755 C5 Lenalidomide-PEG5-NH2 hydrochloride
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911739 C5 Lenalidomide-PEG1-NH2 hydrochloride, ≥95%
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917303 C5 Lenalidomide-C6-PEG1-C3-PEG1-Butyl NH2 hydrochloride, ≥95%
917818 (S,R,S)-AHPC-C9-NH2 hydrochloride, ≥95%
919357 (S,R,S)-AHPC-PEG1-piperazine hydrochloride, ≥95%
919969 C5 Lenalidomide-PEG2-Butyl NH2 hydrochloride, ≥95%

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