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901487

(S,S,S)-AHPC hydrochloride

Name: (S,S,S)-AHPC hydrochloride
Brand: ALDRICH

≥97%

Synonym(s):

(2S,4S)-1-((S)-2-Amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride, E3 Ligase ligand negative control epimer, Ligand for PROTAC^® research, VH032 negative control

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About This Item

Empirical Formula (Hill Notation):

C₂₂H₃₀N₄O₃S · xHCl

CAS Number:

2115897-23-7

Molecular Weight:

430.56 (free base basis)

MDL number:

MFCD32062443

UNSPSC Code:

12352101

NACRES:

NA.22

Assay:

≥97%

Form:

powder or crystals

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Properties

ligand

VH032

Quality Level

100

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

InChI

1S/C22H30N4O3S.ClH/c1-13-18(30-12-25-13)15-7-5-14(6-8-15)10-24-20(28)17-9-16(27)11-26(17)21(29)19(23)22(2,3)4;/h5-8,12,16-17,19,27H,9-11,23H2,1-4H3,(H,24,28);1H/t16-,17-,19+;/m0./s1

InChI key

JYRTWGCWUBURGU-ITJMAPPJSA-N

Description

Application

(S,S,S)-AHPC (HCl salt) is a ligand used as a negative control for (S,R,S)-AHPC (cat# 901490) in the recruitment of the von Hippel–Lindau (VHL) protein for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology.

Other Notes

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Portal: Building PROTAC^® Degraders for Targeted Protein Degradation

Selective Small Molecule Induced Degradation of the BET Bromodomain Protein BRD4

Small-Molecule PROTACS: New Approaches to Protein Degradation

Identification and Characterization of Von Hippel-Lindau-Recruiting Proteolysis Targeting Chimeras (PROTACs) of TANK-Binding Kinase 1

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number

0000399303

MKCR9864

MKCG6337

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Articles

Degrader Building Blocks for Targeted Protein Degradation

Protein Degrader Building Blocks are a collection of crosslinker-E3 ligand conjugates with a pendant functional group for covalent linkage to a target ligand.

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).

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

Identification and Characterization of Von Hippel-Lindau-Recruiting Proteolysis Targeting Chimeras (PROTACs) of TANK-Binding Kinase 1.

Andrew P Crew et al.

Journal of medicinal chemistry, 61(2), 583-598 (2017-07-12)

Proteolysis targeting chimeras (PROTACs) are bifunctional molecules that recruit an E3 ligase to a target protein to facilitate ubiquitination and subsequent degradation of that protein. While the field of targeted degraders is still relatively young, the potential for this modality

Selective Small Molecule Induced Degradation of the BET Bromodomain Protein BRD4.

Michael Zengerle et al.

ACS chemical biology, 10(8), 1770-1777 (2015-06-03)

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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Global Trade Item Number

SKU	GTIN
901487-10MG-KC	04065272217217
901487-10MG	04061834671503
901487-100MG	04065267009216

Key Documents

(S,S,S)-AHPC hydrochloride

≥97%

Select a Size

About This Item

ligand

Quality Level

assay

form

reaction suitability

storage temp.

SMILES string

InChI

InChI key

Application

Other Notes

Legal Information

Safety Information

Storage Class

wgk

flash_point_f

flash_point_c

Regulatory Information

Documentation

Certificates of Analysis (COA)

Already Own This Product?

Protocols and Articles

Articles

Peer Reviewed Papers

Global Trade Item Number