Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

909262

Sigma-Aldrich

(S,R,S)-AHPC-PEG4-Azide

≥95%

Synonym(s):

(2S,4R)-1-((S)-17-Azido-2-(tert-butyl)-4-oxo-6,9,12,15-tetraoxa-3-azaheptadecanoyl)-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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C32H47N7O8S
CAS Number:
1797406-81-5
Molecular Weight:
689.82
UNSPSC Code:
51171641

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(COCCOCCOCCOCCN=[N+]=[N-])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

Application

Protein degrader builiding block (S,R,S)-AHPC-PEG4-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 an alkyne 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 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 Target Warhead and Linkage Vector on Inducing Protein Degradation: Comparison of Bromodomain and Extra-Terminal (BET) Degraders Derived from Triazolodiazepine (JQ1) and Tetrahydroquinoline (I-BET726) BET Inhibitor Scaffolds

Selective Small Molecule Induced Degradation of the BET Bromodomain Protein BRD4

Legal Information

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

related product

Product No.
Description
Pricing

901490

(S,R,S)-AHPC hydrochloride, ≥97%

901487

(S,S,S)-AHPC hydrochloride, ≥97%

901488

(S,R,S)-AHPC-PEG2-NH2 hydrochloride, ≥95%

901493

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

901494

N-Methylated pomalidomide, ≥98%

901495

Pomalidomide-PEG3-NH2 hydrochloride, ≥95%

901496

Pomalidomide-C6-CO2H, ≥98%

901500

Pomalidomide-C3-CO2H, ≥95%

901503

(S,R,S)-AHPC-PEG1-Alkyne, ≥95%

901511

(S,R,S)-AHPC-PEG3-NH2 hydrochloride, ≥95%

901504

Pomalidomide-PEG3-CO2H, ≥95%

901517

(S,R,S)-AHPC-PEG2-Alkyne, ≥95%

901516

Pomalidomide-PEG1-NH2 hydrochloride, ≥95%

901513

Pomalidomide-PEG2-NH2 hydrochloride, ≥95%

901523

Pomalidomide-PEG1-Alkyne, ≥98%

901533

(S,R,S)-AHPC-PEG3-Alkyne, ≥95%

901534

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

901531

Pomalidomide-PEG3-Alkyne, ≥95%

901529

Pomalidomide-PEG2-Alkyne, ≥95%

901527

Pomalidomide-PEG1-CO2H, ≥95%

901526

Pomalidomide-PEG2-CO2H, 95%

901525

Pomalidomide-C9-CO2H, ≥95%

901558

Lenalidomide, ≥95%

901835

Pomalidomide-PEG6-Alkyne

901834

Pomalidomide-PEG5-Alkyne, ≥95%

901833

Pomalidomide-PEG4-Alkyne

901831

Pomalidomide-PEG5-NH2 hydrochloride

901829

Pomalidomide-PEG6-CO2H

901828

Pomalidomide-PEG5-CO2H, ≥95%

901824

Pomalidomide-PEG4-CO2H

901860

(S,R,S)-AHPC-PEG6-NH2 hydrochloride, ≥95%

901855

(S,R,S)-AHPC-PEG5-Alkyne

901851

(S,R,S)-AHPC-PEG4-Alkyne

901850

(S,R,S)-AHPC-PEG5-NH2 hydrochloride

901848

(S,R,S)-AHPC-PEG4-NH2 hydrochloride, ≥95%

901873

(S,R,S)-AHPC-PEG6-Alkyne

903434

Pomalidomide-PEG6-butyl azide, ≥95%

903442

Pomalidomide-PEG6-butyl iodide, ≥95%

903833

Pomalidomide-PEG2-azide

903825

Pomalidomide-PEG1-azide

903957

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

904651

(S,R,S)-AHPC-PEG3-azide, ≥95%

904724

Pomalidomide-PEG2-butyl iodide, ≥95%

904708

Pomalidomide-C6-PEG3-butyl iodide, ≥95%

904678

Pomalidomide-PEG3-azide

904686

Pomalidomide-C6-PEG3-butyl azide, ≥95%

904813

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

904821

(S,R,S)-AHPC-C6-PEG3-butyl azide, ≥95%

904880

Pomalidomide-C6-PEG1-C3-PEG1-butyl azide, ≥95%

904872

Pomalidomide-PEG2-butyl azide, ≥95%

904864

(S,R,S)-AHPC-PEG6-butyl azide, ≥95%

905178

(S,R,S)-AHPC-C6-PEG1-C3-PEG1-butyl azide, ≥95%

905275

(S,R,S)-AHPC-PEG6-butyl amine hydrochloride, ≥95%

905216

(S,R,S)-AHPC-PEG2-butyl azide, ≥95%

905232

(S,R,S)-AHPC-C6-PEG3-butyl amine hydrochloride, ≥95%

905224

Pomalidomide-PEG6-butyl amine hydrochloride, ≥95%

905399

(S,R,S)-AHPC-PEG2-butyl chloride

905380

(S,R,S)-AHPC-C6-PEG3-butyl chloride, ≥95%

905402

(S,R,S)-AHPC-C6-PEG1-C3-PEG1-butyl chloride, 95%

906050

Pomalidomide-C6-PEG1-C3-PEG1-butyl iodide, ≥95%

906123

(S,R,S)-AHPC-PEG2-butyl amine hydrochloride

910449

Pomalidomide-PEG2-butyl CO2H, ≥95%

911801

AHPC-C6-PEG1-C3-PEG1-butyl amine hydrochloride, ≥90%

911690

C5 Lenalidomide, ≥95%

911666

Pomalidomide-C6-NH2 hydrochloride, ≥95%

911658

Pomalidomide-C3-NH2 hydrochloride, ≥95%

911763

C5 Lenalidomide-PEG1-piperazine hydrochloride, ≥95%

913987

Pomalidomide-C6-PEG1-C3-PEG1-butyl amine hydrochloride, ≥95%

915572

Pomalidomide-dipiperazine-NH2 hydrochloride, ≥95%

916536

Pomalidomide-piperazine-pyridine-alkyne-NH2 hydrochloride

917729

C5 Lenalidomide-piperazine-pyridine-alkyne-NH2 hydrochloride, ≥95%

917303

C5 Lenalidomide-C6-PEG1-C3-PEG1-Butyl NH2 hydrochloride, ≥95%

917818

(S,R,S)-AHPC-C9-NH2 hydrochloride, ≥95%

919357

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

918687

(S,R,S)-AHPC-alkyne-piperidine hydrochloride

919969

C5 Lenalidomide-PEG2-Butyl NH2 hydrochloride, ≥95%

919896

C5 Lenalidomide-dipiperazine-NH2 hydrochloride

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCL2943

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Michael Zengerle et al.
ACS chemical biology, 10(8), 1770-1777 (2015-06-03)
The Bromo- and Extra-Terminal (BET) proteins BRD2, BRD3, and BRD4 play important roles in transcriptional regulation, epigenetics, and cancer and are the targets of pan-BET selective bromodomain inhibitor JQ1. However, the lack of intra-BET selectivity limits the scope of current
Kwok-Ho Chan et al.
Journal of medicinal chemistry, 61(2), 504-513 (2017-06-09)
The design of proteolysis-targeting chimeras (PROTACs) is a powerful small-molecule approach for inducing protein degradation. PROTACs conjugate a target warhead to an E3 ubiquitin ligase ligand via a linker. Here we examined the impact of derivatizing two different BET bromodomain
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
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
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

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.

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.

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.

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service