Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

919454

Sigma-Aldrich

CCW16-PEG3-BocNH

≥95%

Synonym(s):

tert-Butyl (2-(2-(2-(2-(4-(4-(N-Benzyl-2-chloroacetamido)phenoxy)phenoxy)ethoxy)ethoxy)ethoxy)ethyl)carbamate, Crosslinker-E3 Ligase ligand conjugate, Protein degrader building block for PROTAC® research, RNF4-targeting building block, Template for synthesis of targeted protein degrader

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

About This Item

Empirical Formula (Hill Notation):
C34H43ClN2O8
Molecular Weight:
643.17
NACRES:
NA.22

ligand

CCW16

Quality Level

100

Assay

≥95%

form

liquid

reaction suitability

reactivity: carboxyl reactive
reagent type: ligand-linker conjugate

functional group

amine

storage temp.

2-8°C

SMILES string

O=C(CCl)N(CC1=CC=CC=C1)C2=CC=C(C=C2)OC3=CC=C(OCCOCCOCCOCCNC(OC(C)(C)C)=O)C=C3

Application

Protein degrader building block CCW16-PEG3-BocNH enables the synthesis of molecules for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. This conjugate contains a RING finger protein 4 (RNF4)-recruiting ligand, a PEGylated crosslinker, and a pendant amine for reactivity with a carboxylic acid 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 terminal amine, 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

Covalent Ligand Screening Uncovers a RNF4 E3 Ligase Recruiter for Targeted Protein Degradation Applications

Targeted Protein Degradation by Small Molecules

Small-Molecule PROTACS: New Approaches to Protein Degradation

Targeted Protein Degradation: from Chemical Biology to Drug Discovery

Legal Information

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

related product

Product No.
Description
Pricing

901495

Pomalidomide-PEG3-NH2 hydrochloride, ≥95%

901511

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

901504

Pomalidomide-PEG3-CO2H, ≥95%

901533

(S,R,S)-AHPC-PEG3-Alkyne, ≥95%

901531

Pomalidomide-PEG3-Alkyne, ≥95%

904651

(S,R,S)-AHPC-PEG3-azide, ≥95%

904678

Pomalidomide-PEG3-azide

911747

C5 Lenalidomide-PEG3-NH2 hydrochloride, ≥95%

917680

BocA1V1PF2-OPEG3-NH2 hydrochloride

917702

A1V2PF1-NHEt-PEG3-NH2

917214

BocA1V2PF1-NHPEG3-NH2, ≥85%

916676

A1V1PF2-OEt-PEG3-NH2 hydrochloride

916692

BocA1V2PF2-NHPEG3-NH2, ≥95%

917192

A1V2PF2-NHEt-PEG3-NH2, ≥95%

919438

CCW16-C9-BocNH, ≥95%

919470

CCW16-PEG2-butyl-BocNH, ≥95%

919462

CCW16-PEG5-BocNH, ≥95%

919403

CCW16-C4-BocNH, 95%

919446

CCW16-PEG1-BocNH

919489

CCW16-C6-PEG3-butyl-BocNH

919411

CCW16-C6-BocNH

919381

CCW16, ≥95%

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

Sorry, we don't have COAs for this product available online at this time.

If you need assistance, please contact Customer Support.

Already Own This Product?

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

Visit the Document Library

Carl C Ward et al.
ACS chemical biology, 14(11), 2430-2440 (2019-05-07)
Targeted protein degradation has arisen as a powerful strategy for drug discovery allowing the targeting of undruggable proteins for proteasomal degradation. This approach most often employs heterobifunctional degraders consisting of a protein-targeting ligand linked to an E3 ligase recruiter to
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
Daniel P Bondeson et al.
Annual review of pharmacology and toxicology, 57, 107-123 (2016-10-13)
Protein homeostasis networks are highly regulated systems responsible for maintaining the health and productivity of cells. Whereas therapeutics have been developed to disrupt protein homeostasis, more recently identified techniques have been used to repurpose homeostatic networks to effect degradation of
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