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901850

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

Synonym(s):

(2S,4R)-1-((S)-20-Amino-2-(tert-butyl)-4-oxo-6,9,12,15,18-pentaoxa-3-azaicosanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride, Crosslinker−E3 ligase ligand conjugate, Protein degrader building block for PROTAC® research, Template for synthesis of targeted protein degrader, VH032 conjugate

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About This Item

Empirical Formula (Hill Notation):
C34H54ClN5O9S
Molecular Weight:
744.34
MDL number:
MFCD32173797
UNSPSC Code:
12352101
NACRES:
NA.22
Form:
crystals
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ligand

VH032

form

crystals

reaction suitability

reactivity: carboxyl reactive, reagent type: ligand-linker conjugate

functional group

amine

storage temp.

2-8°C

SMILES string

O=C(COCCOCCOCCOCCOCCN)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.Cl

InChI

1S/C34H53N5O9S.ClH/c1-24-30(49-23-37-24)26-7-5-25(6-8-26)20-36-32(42)28-19-27(40)21-39(28)33(43)31(34(2,3)4)38-29(41)22-48-18-17-47-16-15-46-14-13-45-12-11-44-10-9-35;/h5-8,23,27-28,31,40H,9-22,35H2,1-4H3,(H,36,42)(H,38,41);1H/t27-,28+,31-;/m1./s1

InChI key

FJDKQBVZPSNEBT-LJGPDLSOSA-N

Application

Protein degrader building block (SRS)-AHPC-PEG5-NH2 (HCl salt) 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 and a PEGylated crosslinker with pendant amine for reactivity with a carboxyl group 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 amine parallel synthesis can be used to more quickly generate PROTAC libraries that feature variation in crosslinker length composition and E3 ligase ligand.

Automate your VHL-PEG based PROTACs with Synple Automated Synthesis Platform (SYNPLE-SC002)

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 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

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL7449

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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.

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
Kedra Cyrus et al.
Molecular bioSystems, 7(2), 359-364 (2010-10-06)
Conventional genetic approaches have provided a powerful tool in the study of proteins. However, these techniques often preclude selective manipulation of temporal and spatial protein functions, which is crucial for the investigation of dynamic cellular processes. To overcome these limitations
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Global Trade Item Number

SKUGTIN
901850-50MG04061835334186