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929352

Sigma-Aldrich

(S,R,S)-AHPC-di-trimethylamide-dioxodisulfide-carbonate ester

Synonym(s):

S-(1-(((((3R,5S)-1-((S)-2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoyl)-5-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-3-yl)oxy)carbonyl)oxy)-2-methylpropan-2-yl) methanesulfonothioate

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About This Item

Empirical Formula (Hill Notation):
C33H48N4O9S3
CAS Number:
2417370-08-0
Molecular Weight:
740.95
UNSPSC Code:
12352108
NACRES:
NA.21

ligand

VH032

Assay

≥95%

form

powder

functional group

disulfide

storage temp.

2-8°C

SMILES string

CC(C)(C)OC(N[C@@H](C(C)(C)C)C(N1[C@@H](C[C@H](C1)OC(OCC(C)(C)SS(C)(=O)=O)=O)C(NCC2=CC=C(C3=C(C)N=CS3)C=C2)=O)=O)=O

Application

Protein degrader building block (S,R,S)-AHPC-di-trimethylamide-dioxodisulfide-carbonate ester 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 and a pendant disulfide, linked via a carbonate group. The pendant disulfide allows for targeted degradation of antibodies. 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

Antibody Conjugation of a Chimeric BET Degrader Enables in vivo Activity

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

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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

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