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Merck
CN

904864

(S,R,S)-AHPC-PEG6-butyl azide

≥95%

Synonym(s):

(2S,4R)-1-((S)-27-Azido-2-(tert-butyl)-4-oxo-6,9,12,15,18,21-hexaoxa-3-azaheptacosanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide, (S,R,S)-AHPC-2-2-2-2-2-2-6-N3, 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

Empirical Formula (Hill Notation):
C40H63N7O10S
Molecular Weight:
834.03
MDL number:
MFCD32173808
UNSPSC Code:
51171641
NACRES:
NA.22

Key Documents

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ligand

VH032

Assay

≥95%

form

liquid

reaction suitability

reaction type: click chemistry
reagent type: ligand-linker conjugate

functional group

azide

storage temp.

2-8°C

SMILES string

O=C(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)COCCOCCOCCOCCOCCOCCCCCCN=[N+]=[N-]

InChI

1S/C40H63N7O10S/c1-30-36(58-29-43-30)32-11-9-31(10-12-32)26-42-38(50)34-25-33(48)27-47(34)39(51)37(40(2,3)4)45-35(49)28-57-24-23-56-22-21-55-20-19-54-18-17-53-16-15-52-14-8-6-5-7-13-44-46-41/h9-12,29,33-34,37,48H,5-8,13-28H2,1-4H3,(H,42,50)(H,45,49)/t33-,

InChI key

AZGJMFKKWCUJTE-WYMKREKISA-N

Related Categories

Application

Protein degrader builiding block (S,R,S)-AHPC-PEG6-butyl azide 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 azide for click chemistry with 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 azide group, 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

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCJ2617

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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.

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