Skip to Content
Merck
All Photos(1)

Key Documents

More Documents

929344

Sigma-Aldrich

(S,R,S)-AHPC-C5-phosphoramidite

Synonym(s):

(3R,5S)-1-((2S)-2-(6-(((2-Cyanoethoxy)(diisopropylamino)phosphaneyl)oxy)hexanamido)-3,3-dimethylbutanoyl)-5-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-3-yl acetate

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

About This Item

Empirical Formula (Hill Notation):
C39H59N6O7PS
Molecular Weight:
786.96

form

solid or liquid

Quality Level

100

storage temp.

2-8°C

SMILES string

O=C(N1C[C@H](OC(C)=O)C[C@H]1C(NCC2=CC=C(C3=C(C)N=CS3)C=C2)=O)[C@H](C(C)(C)C)NC(CCCCCOP(OCCC#N)N(C(C)C)C(C)C)=O

Related Categories

Application

Protein degrader building block (S,R,S)-AHPC-C5-phosphoramidite enables the synthesis of molecules for degradation of proteins and PROTAC® (proteolysis-targeting chimeras) research. This conjugate contains a von Hippel-Lindau (VHL)-recruiting ligand, a rigid linker, and a pendant phosphoramidite for reactivity with target DNA-binding proteins such as transcription factors. Because even slight alterations in ligands and crosslinkers can affect ternary complex formation between the target, E3 ligase, and degrader, many analogs are prepared to screen for optimal target degradation. When used with other protein degrader building blocks, parallel synthesis can be used to more quickly generate degrader libraries that feature variation in crosslinker length, composition, and E3 ligase ligand.

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Protein Degrader Building Blocks

Other Notes

Targeted Protein Degradation by Small Molecules

Destruction of DNA-Binding Proteins by Programmable Oligonucleotide PROTAC (O′PROTAC): Effective Targeting of LEF1 and ERG

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

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

Visit the Document Library

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

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