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Merck
CN

921432

(S,R,S)-AHPC-pyridine-PEG1-piperazine hydrochloride

Synonym(s):

(2S,4R)-1-[(2S)-3,3-dimethyl-2-(2-{6-[3-(piperazin-1-yl)propoxy]pyridin-3-yl}acetamido)butanoyl]-4-hydroxy-N-{[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl}pyrrolidine-2-carboxamide, Crosslinker−E3 Ligase ligand conjugate, Protein degrader building block for PROTAC® research, Template for synthesis of targeted protein degrader, VH032 conjugate hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C36H49N7O5S · xHCl
Molecular Weight:
691.88 (free base basis)
MDL number:
MFCD34549950
UNSPSC Code:
12352200
NACRES:
NA.22

Key Documents

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ligand

VH032

Quality Level

100

form

solid

reaction suitability

reactivity: carboxyl reactive
reagent type: ligand-linker conjugate

functional group

amine

storage temp.

2-8°C

SMILES string

CC(N=CS1)=C1C2=CC=C(CNC([C@@H]3C[C@@H](O)CN3C([C@@H](NC(CC4=CC=C(OCCCN5CCNCC5)N=C4)=O)C(C)(C)C)=O)=O)C=C2.Cl

InChI

1S/C36H49N7O5S.ClH/c1-24-32(49-23-40-24)27-9-6-25(7-10-27)20-39-34(46)29-19-28(44)22-43(29)35(47)33(36(2,3)4)41-30(45)18-26-8-11-31(38-21-26)48-17-5-14-42-15-12-37-13-16-42;/h6-11,21,23,28-29,33,37,44H,5,12-20,22H2,1-4H3,(H,39,46)(H,41,45);1H/t28-,29+,33-

InChI key

NDWOOCSZWCUODV-FQIZLRTDSA-N

Related Categories

Application

Protein degrader building block (S,R,S)-AHPC-pyridine-PEG1-piperazine 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, a linker, and a pendant amine for reactivity with a carboxylic acid on the 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 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

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

Storage Class Code

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
0000126434
0000126434
0000123387

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Daniel P Bondeson et al.
Annual review of pharmacology and toxicology, 57, 107-123 (2016-10-13)
Protein homeostasis networks are highly regulated systems responsible for maintaining the health and productivity of cells. Whereas therapeutics have been developed to disrupt protein homeostasis, more recently identified techniques have been used to repurpose homeostatic networks to effect degradation of
Kedra Cyrus et al.
Molecular bioSystems, 7(2), 359-364 (2010-10-06)
Conventional genetic approaches have provided a powerful tool in the study of proteins. However, these techniques often preclude selective manipulation of temporal and spatial protein functions, which is crucial for the investigation of dynamic cellular processes. To overcome these limitations
Momar Toure et al.
Angewandte Chemie (International ed. in English), 55(6), 1966-1973 (2016-01-13)
The current inhibitor-based approach to therapeutics has inherent limitations owing to its occupancy-based model: 1) there is a need to maintain high systemic exposure to ensure sufficient in vivo inhibition, 2) high in vivo concentrations bring potential for off-target side effects, and 3) there is
Philipp M Cromm et al.
Cell chemical biology, 24(9), 1181-1190 (2017-06-27)
Traditional pharmaceutical drug discovery is almost exclusively focused on directly controlling protein activity to cure diseases. Modulators of protein activity, especially inhibitors, are developed and applied at high concentration to achieve maximal effects. Thereby, reduced bioavailability and off-target effects can

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.

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