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905380

Sigma-Aldrich

(S,R,S)-AHPC-C6-PEG3-butyl chloride

≥95%

Synonym(e):

(2S,4R)-1-((S)-2-(tert-Butyl)-22-chloro-4-oxo-10,13,16-trioxa-3-azadocosanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide, (S,R,S)-AHPC-6-2-2-6-Cl, Crosslinker−E3 Ligase ligand conjugate, Protein degrader building block for PROTAC® research, Template for synthesis of targeted protein degrader, VH032 conjugate

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About This Item

Empirische Formel (Hill-System):
C38H59ClN4O7S
CAS-Nummer:
1835705-55-9
Molekulargewicht:
751.42
MDL-Nummer:
MFCD31560478
UNSPSC-Code:
12352101
NACRES:
NA.22

ligand

VH032

Assay

≥95%

Form

solid

Eignung der Reaktion

reactivity: sulfuryl reactive
reagent type: ligand-linker conjugate

Funktionelle Gruppe

alkyl halide

Lagertemp.

2-8°C

SMILES String

ClCCCCCCOCCOCCOCCCCCC(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)=O

Verwandte Kategorien

Anwendung

Protein degrader builiding block (S,R,S)-AHPC-C6-PEG3-butyl Chloride 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 with both hydrophobic and hydrophilic moieties, and a pendant chloroalkane for reactivity with a nucleophilic group on a 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 pendant chloro group, parallel synthesis can be used to more quickly generate PROTAC libraries that feature variation in crosslinker length, composition, and E3 ligase ligand.

Sonstige Hinweise

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Portal: Building PROTAC® Degraders for Targeted Protein Degradation

Modular PROTAC Design for the Degradation of Oncogenic BCR-ABL

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

Rechtliche Hinweise

PROTAC is a registered trademark of Arvinas Operations, Inc., and is used under license

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WGK

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Flammpunkt (°F)

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Flammpunkt (°C)

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Analysenzertifikate (COA)

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(S,R,S)-AHPC-C6-CO2H hydrochloride

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(S,R,S)-AHPC-PEG6-NH2 hydrochloride

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Sigma-Aldrich

901490

(S,R,S)-AHPC hydrochloride

(S,R,S)-AHPC-PEG2-azide

Sigma-Aldrich

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(S,R,S)-AHPC-PEG2-azide

(S,R,S)-AHPC-PEG1-NH2 hydrochloride ≥95%

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901493

(S,R,S)-AHPC-PEG1-NH2 hydrochloride

(S,R,S)-AHPC-PEG3-azide ≥95%

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(S,R,S)-AHPC-PEG3-azide

Ashton C Lai et al.
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
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
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
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
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

Artikel

Degrader Building Blocks for Targeted Protein Degradation

Partial PROTACs are a collection of crosslinker-E3 ligand conjugates with a pendant functional group for covalent linkage to a target ligand.

Partial PROTACs for Targeted Protein Degradation

Partial PROTACs are a collection of crosslinker-E3 ligand conjugates with a pendant functional group for covalent linkage to a target ligand.

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