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Merck
CN

903957

(S,R,S)-AHPC-PEG1-azide

Synonym(s):

(2S,4R)-1-((S)-2-(2-(2-Azidoethoxy)acetamido)-3,3-dimethylbutanoyl)-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, VH032 conjugate

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About This Item

Empirical Formula (Hill Notation):
C26H35N7O5S
CAS Number:
2101200-09-1
Molecular Weight:
557.67
MDL number:
MFCD31807301
UNSPSC Code:
51171641
NACRES:
NA.22

Key Documents

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InChI

1S/C26H35N7O5S/c1-16-22(39-15-29-16)18-7-5-17(6-8-18)12-28-24(36)20-11-19(34)13-33(20)25(37)23(26(2,3)4)31-21(35)14-38-10-9-30-32-27/h5-8,15,19-20,23,34H,9-14H2,1-4H3,(H,28,36)(H,31,35)/t19-,20+,23-/m1/s1

InChI key

YVCURZJBLHZABY-ZRCGQRJVSA-N

SMILES string

O=C(NCC1=CC=C(C2=C(C)N=CS2)C=C1)[C@H](C[C@@H](O)C3)N3C([C@H](C(C)(C)C)NC(COCCN=[N+]=[N-])=O)=O

ligand

VH032

assay

≥95%

form

powder

reaction suitability

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

functional group

azide

storage temp.

2-8°C

Related Categories

Application

Protein degrader builiding block (S,R,S)-AHPC-PEG1-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 and a PEGylated crosslinker with 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.

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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Certificates of Analysis (COA)

Lot/Batch Number
0000145450
0000104550
MKCJ0500

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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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