901490
(S,R,S)-AHPC hydrochloride
≥97%
Synonym(s):
(2S,4R)-1-((S)-2-Amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride, E3 Ligase ligand, Ligand for PROTAC® research, VH032
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About This Item
Empirical Formula (Hill Notation):
C22H30N4O3S · xHCl
CAS Number:
Molecular Weight:
430.56 (free base basis)
MDL number:
UNSPSC Code:
12352101
NACRES:
NA.22
Recommended Products
ligand
VH032
Quality Level
Assay
≥97%
form
powder or crystals
reaction suitability
reagent type: ligand
storage temp.
2-8°C
SMILES string
N[C@H](C(N1[C@H](C(NCC2=CC=C(C3=C(C)N=CS3)C=C2)=O)C[C@@H](O)C1)=O)C(C)(C)C.Cl
Application
(S,R,S)-AHPC (HCl salt) is a ligand used in the recruitment of the von Hippel-Lindau (VHL) protein for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. This (S,R,S) conformation is the active variant, and (S,S,S) is the inactive derivative (cat#901487) used as a negative control.
Other Notes
Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation
Portal: Building PROTAC® Degraders for Targeted Protein Degradation
Structure-Guided Design and Optimization of Small Molecules Targeting the Protein-Protein Interaction between the von Hippel-Lindau (VHL) E3 Ubiquitin Ligase and the Hypoxia Inducible Factor (HIF) Alpha Subunit with in Vitro Nanomolar Affinities
Modular PROTAC Design for the DegradationofOncogenic BCR-ABL
Selective Small Molecule Induced Degradation of the BET Bromodomain Protein BRD4
Group-Based Optimization of Potent and Cell-Active Inhibitors of the von Hippel–Lindau (VHL) E3 Ubiquitin Ligase: Structure–Activity Relationships Leading to the Chemical Probe (2S,4R)-1-((S)-2-(1-Cyanocyclopropanecarboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (VH298)
Portal: Building PROTAC® Degraders for Targeted Protein Degradation
Structure-Guided Design and Optimization of Small Molecules Targeting the Protein-Protein Interaction between the von Hippel-Lindau (VHL) E3 Ubiquitin Ligase and the Hypoxia Inducible Factor (HIF) Alpha Subunit with in Vitro Nanomolar Affinities
Modular PROTAC Design for the DegradationofOncogenic BCR-ABL
Selective Small Molecule Induced Degradation of the BET Bromodomain Protein BRD4
Group-Based Optimization of Potent and Cell-Active Inhibitors of the von Hippel–Lindau (VHL) E3 Ubiquitin Ligase: Structure–Activity Relationships Leading to the Chemical Probe (2S,4R)-1-((S)-2-(1-Cyanocyclopropanecarboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (VH298)
Legal Information
PROTAC is a registered trademark of Arvinas Operations, Inc., and is used under license
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Product No.
Description
Pricing
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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Pedro Soares et al.
Journal of medicinal chemistry, 61(2), 599-618 (2017-08-31)
The von Hippel-Lindau tumor suppressor protein is the substrate binding subunit of the VHL E3 ubiquitin ligase, which targets hydroxylated α subunit of hypoxia inducible factors (HIFs) for ubiquitination and subsequent proteasomal degradation. VHL is a potential target for treating
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The Bromo- and Extra-Terminal (BET) proteins BRD2, BRD3, and BRD4 play important roles in transcriptional regulation, epigenetics, and cancer and are the targets of pan-BET selective bromodomain inhibitor JQ1. However, the lack of intra-BET selectivity limits the scope of current
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Journal of medicinal chemistry, 57(20), 8657-8663 (2014-08-29)
E3 ubiquitin ligases are attractive targets in the ubiquitin-proteasome system, however, the development of small-molecule ligands has been rewarded with limited success. The von Hippel-Lindau protein (pVHL) is the substrate recognition subunit of the VHL E3 ligase that targets HIF-1α
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Angewandte Chemie (International ed. in English), 55(2), 807-810 (2015-11-26)
Proteolysis Targeting Chimera (PROTAC) technology is a rapidly emerging alternative therapeutic strategy with the potential to address many of the challenges currently faced in modern drug development programs. PROTAC technology employs small molecules that recruit target proteins for ubiquitination and
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