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901851

(S,R,S)-AHPC-PEG₄-Alkyne

Name: (S,R,S)-AHPC-PEG4-Alkyne
Brand: ALDRICH

Synonym(s):

(2S,4R)-1-((S)-2-(tert-Butyl)-4-oxo-7,10,13,16-tetraoxa-3-azanonadec-18-ynoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide, Crosslinker−E3 Ligase ligand conjugate, Protein degrader building block for PROTAC^® research, Template for synthesis of targeted protein degrader

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About This Item

Empirical Formula (Hill Notation):

C₃₄H₄₈N₄O₈S

Molecular Weight:

672.83

MDL number:

MFCD32173798

UNSPSC Code:

51171641

NACRES:

NA.22

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Properties

ligand

VH032

Quality Level

200

form

solid

reaction suitability

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

functional group

alkyne

storage temp.

2-8°C

SMILES string

O=C(CCOCCOCCOCCOCC#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

InChI

1S/C34H48N4O8S/c1-6-12-43-14-16-45-18-19-46-17-15-44-13-11-29(40)37-31(34(3,4)5)33(42)38-22-27(39)20-28(38)32(41)35-21-25-7-9-26(10-8-25)30-24(2)36-23-47-30/h1,7-10,23,27-28,31,39H,11-22H2,2-5H3,(H,35,41)(H,37,40)/t27-,28+,31-/m1/s1

InChI key

FTLDORQHAGSPKF-CKIYMEHHSA-N

Description

Application

Protein degrader builiding block (S,R,S)-AHPC-PEG₄-Alkyne 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 and a PEGylated crosslinker with pendant alkyne for click chemistry with an azide 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 pendant alkyne group, parallel synthesis can be used to more quickly generate PROTAC libraries that feature variation in crosslinker length, composition, and E3 ligase ligand.

Automate your VHL-PEG based PROTACs with Synple Automated Synthesis Platform (SYNPLE-SC002)

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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