(S,R,S)-AHPC-Me hydrochloride

 CAS No.: 1948273-03-7  Cat No.: BP-200017 4.5  

(S,R,S)-AHPC-Me hydrochloride is a specialized E3 Ligase Ligand optimized for use in the synthesis of PROTACs (Proteolysis Targeting Chimeras). This compound selectively binds to the von Hippel-Lindau (VHL) E3 ubiquitin ligase, facilitating the recruitment of VHL to the target protein for ubiquitination and subsequent proteasomal degradation. By leveraging its high affinity and selectivity, (S,R,S)-AHPC-Me hydrochloride enables researchers to develop targeted VHL-based PROTACs for precise protein degradation, accelerating drug discovery and chemical biology studies. It is a vital tool for constructing bifunctional molecules aimed at regulating disease-associated proteins, expanding the possibilities in targeted protein degradation research and therapeutic development.

(S,R,S)-AHPC-Me hydrochloride

Structure of 1948273-03-7

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Category
Ligand for E3 Ligase
Molecular Formula
C23H33ClN4O3S
Molecular Weight
481.05

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

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Solubility
DMSO : ≥ 63 mg/mL
Storage
Powder, -20°C, 3 years; 4°C, 2 years; In solvent, -80°C, 6 months; -20°C, 1 month
Shipping
Room temperature in continental US; may vary elsewhere
IUPACName
(2S,4R)-1-[(2S)-2-amino-3,3-dimethylbutanoyl]-4-hydroxy-N-[(1S)-1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]ethyl]pyrrolidine-2-carboxamide;hydrochloride
Synonyms
VHL ligand 2 (hydrochloride); E3 ligase Ligand 1
InChI Key
GHFOLQCCYGBOTL-QDVBFIRISA-N
InChI
InChI=1S/C23H32N4O3S.ClH/c1-13(15-6-8-16(9-7-15)19-14(2)25-12-31-19)26-21(29)18-10-17(28)11-27(18)22(30)20(24)23(3,4)5;/h6-9,12-13,17-18,20,28H,10-11,24H2,1-5H3,(H,26,29);1H/t13-,17+,18-,20+;/m0./s1
Canonical SMILES
CC1=C(SC=N1)C2=CC=C(C=C2)C(C)NC(=O)C3CC(CN3C(=O)C(C(C)(C)C)N)O.Cl

Background Introduction

(S,R,S)-AHPC-Me hydrochloride is a potent, selective ligand for the von Hippel-Lindau (VHL) E3 ubiquitin ligase. As a key building block in the synthesis of PROTAC molecules, (S,R,S)-AHPC-Me hydrochloride provides high affinity binding to the VHL protein, making it an essential tool for targeted protein degradation research in chemical biology and drug discovery. Its methyl modification and stereochemistry facilitate optimized linkage strategies and pharmacokinetic properties.

Mechanism

(S,R,S)-AHPC-Me hydrochloride functions by binding specifically to the VHL component of the CRL2VHL E3 ligase complex. When incorporated into a PROTAC, the molecule anchors the E3 ligase in proximity to a target protein, which is simultaneously recognized by the PROTAC's target ligand moiety. This induced proximity facilitates the transfer of ubiquitin from the E2 enzyme to the target protein, tagging it for rapid proteasomal degradation. The precise stereochemistry of (S,R,S)-AHPC-Me enhances interaction fidelity and degradation efficacy.

Applications

(S,R,S)-AHPC-Me hydrochloride is widely employed in VHL-based PROTAC design for selective degradation of disease-relevant proteins. Key applications include:

• Construction of VHL ligand-linker conjugates in PROTACs for chemical biology studies and therapeutic development
• Synthesis of bifunctional degraders targeting kinases, transcriptional regulators, and epigenetic proteins
• Structure-activity relationship (SAR) work to optimize ligand orientation and potency in PROTAC platforms
• Customizable linker attachment sites, supporting next-generation toolkit and preclinical pipeline projects in both industry and academia
• High-purity compound verified by HPLC, NMR, and LC-MS
• Consistent batch-to-batch reproducibility with complete QC documentation
• Supplied with COA, MSDS, and analytical data for traceability
• Reliable global shipping with stability-guaranteed packaging
• Dedicated technical support and optional custom synthesis service
• Demonstrates strong binding affinity to CRBN, VHL, or other E3 ligases
• Enables stable E3 ligase recruitment for targeted protein degradation
• Highly selective VHL E3 ligase ligand enables precise protein degradation in PROTAC design.
• Hydrochloride salt form improves solubility, facilitating efficient chemical synthesis and biological evaluation.

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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
g
Historical Records: (S,R,S)-AHPC-Me hydrochloride

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