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901488

(S,R,S)-AHPC-PEG2-NH2 hydrochloride

≥95%

Synonyme(s) :

(2S,4R)-1-((S)-2-(2-(2-(2-Aminoethoxy)ethoxy)acetamido)-3,3-dimethylbutanoyl)-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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A propos de cet article

Formule empirique (notation de Hill) :
C28H41N5O6S · xHCl
Numéro CAS:
2097973-72-1
Poids moléculaire :
575.72 (free base basis)
MDL number:
MFCD32111682
UNSPSC Code:
12352101
NACRES:
NA.22
Assay:
≥95%
Form:
powder or crystals
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ligand

VH032

Quality Level

100

assay

≥95%

form

powder or crystals

reaction suitability

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

functional group

amine

storage temp.

2-8°C

SMILES string

O=C(NCC1=CC=C(C2=C(C)N=CS2)C=C1)[C@H](C[C@@H](O)C3)N3C([C@H](C(C)(C)C)NC(COCCOCCN)=O)=O.Cl

InChI

1S/C28H41N5O6S.ClH/c1-18-24(40-17-31-18)20-7-5-19(6-8-20)14-30-26(36)22-13-21(34)15-33(22)27(37)25(28(2,3)4)32-23(35)16-39-12-11-38-10-9-29;/h5-8,17,21-22,25,34H,9-16,29H2,1-4H3,(H,30,36)(H,32,35);1H/t21-,22+,25-;/m1./s1

InChI key

SYAOHFUUVWFWJH-ZBXLSASTSA-N

Application

Protein degrader builiding block (S,R,S)-AHPC-PEG2-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

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

Degradation of the BAF Complex Factor BRD9 by Heterobifunctional Ligands

Targeted Protein Degradation by Small Molecules

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Classe de stockage

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

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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.

David Remillard et al.
Angewandte Chemie (International ed. in English), 56(21), 5738-5743 (2017-04-19)
The bromodomain-containing protein BRD9, a subunit of the human BAF (SWI/SNF) nucleosome remodeling complex, has emerged as an attractive therapeutic target in cancer. Despite the development of chemical probes targeting the BRD9 bromodomain, there is a limited understanding of BRD9
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
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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Numéro d'article de commerce international

RéférenceGTIN
901488-50MG04061834671510