Name: (S,R,S)-AHPC-PEG1-azide
Brand: BOC Sciences
Price: 499 USD
Availability: MadeToOrder

Size

Price

Stock

Quantity

100 mg

$499

In stock

1 g

$2690

In stock

ShelfLife

2 years

Storage

-20°C

IUPACName

(2S,4R)-1-[(2S)-2-[[2-(2-azidoethoxy)acetyl]amino]-3,3-dimethylbutanoyl]-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide

Synonyms

E3 ligase Ligand-Linker Conjugates 3; (S,R,S)-AHPC-PEG1-N3; (2S,4R)-1-((S)-2-(2-(2-Azidoethoxy)acetamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide

InChI Key

YVCURZJBLHZABY-ZRCGQRJVSA-N

InChI

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

Canonical SMILES

CC1=C(SC=N1)C2=CC=C(C=C2)CNC(=O)C3CC(CN3C(=O)C(C(C)(C)C)NC(=O)COCCN=[N+]=[N-])O

Background Introduction

(S,R,S)-AHPC-PEG1-azide is a specialized E3 ligase ligand-linker conjugate designed for use in targeted protein degradation applications. By incorporating AHPC (hydroxyproline-based ligand) for recruiting the von Hippel-Lindau (VHL) E3 ubiquitin ligase, this molecule is optimized for the construction of PROTACs (Proteolysis Targeting Chimeras). The PEG1 (polyethylene glycol) spacer and terminal azide group enable straightforward conjugation to diverse protein-targeting ligands via click chemistry, facilitating the development of custom PROTAC molecules.

Mechanism

The mechanism of (S,R,S)-AHPC-PEG1-azide centers on its ability to recruit the VHL E3 ubiquitin ligase by mimicking the natural substrate hydroxyproline residue. Upon conjugation to a protein-binding ligand (such as a small molecule or peptide), (S,R,S)-AHPC-PEG1-azide forms a bifunctional PROTAC molecule. This PROTAC bridges the targeted protein of interest with VHL, inducing ubiquitination and subsequent degradation of the target protein by the 26S proteasome. The PEG1 linker provides optimal spatial orientation, while the azide group allows rapid, high-yielding conjugation through azide-alkyne click chemistry.

Applications

(S,R,S)-AHPC-PEG1-azide is an essential research tool for generating custom small-molecule degraders in drug discovery and chemical biology. Its primary applications include:

(1) Construction of novel PROTACs targeting a wide variety of disease-related proteins,

(2) Functional evaluation of protein knockdown effects in cell-based assays and animal models

(3) The development of next-generation degraders with improved selectivity, bioavailability, and pharmacokinetic profiles.

This reagent is invaluable for academic and pharmaceutical researchers seeking to expand targeted protein degradation strategies.

• Azide-functionalized PEG linker enables efficient and versatile click chemistry conjugation with target-binding ligands.
• Designed for high affinity binding to VHL E3 ligase, facilitating potent and selective PROTAC assembly.

Stock concentration: *

Desired final volume: *

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂