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929336

Sigma-Aldrich

Pomalidomide-C5-phosphoramidite

Sinônimo(s):

2-Cyanoethyl (5-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)pentyl) diisopropylphosphoramidite

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About This Item

Fórmula empírica (Notação de Hill):
C27H38N5O6P
Peso molecular:
559.59
Número MDL:
MFCD34704570
Código UNSPSC:
12352101
NACRES:
NA.21

ligand

pomalidomide

Nível de qualidade

100

Formulário

powder

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

O=C1C2=C(C(NCCCCCOP(OCCC#N)N(C(C)C)C(C)C)=CC=C2)C(N1C3C(NC(CC3)=O)=O)=O

InChI

1S/C27H38N5O6P/c1-18(2)32(19(3)4)39(38-17-9-14-28)37-16-7-5-6-15-29-21-11-8-10-20-24(21)27(36)31(26(20)35)22-12-13-23(33)30-25(22)34/h8,10-11,18-19,22,29H,5-7,9,12-13,15-17H2,1-4H3,(H,30,33,34)

chave InChI

LDWPFUQTEOHLBX-UHFFFAOYSA-N

Categorias relacionadas

Aplicação

Protein degrader building block Pomalidomide-C5-phosphoramidite enables the synthesis of molecules for targeted protein degradation and PROTAC® (proteolysis-targeting chimeras) research. This conjugate contains a Cereblon (CRBN) 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

Outras notas

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

Informações legais

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

Pictogramas

Health hazard
GHS08

Palavra indicadora

Danger

Frases de perigo

H360D

Classificações de perigo

Repr. 1B

Código de classe de armazenamento

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

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Certificados de análise (COA)

Lot/Batch Number
0000204809
0000173909
0000204809
0000173909

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Destruction of DNA-Binding Proteins by Programmable Oligonucleotide PROTAC (O'PROTAC): Effective Targeting of LEF1 and ERG
Jingwei Shao, et al.
Advanced science (Weinheim, Baden-Wurttemberg, Germany) (2021)
Jingwei Shao et al.
Advanced science (Weinheim, Baden-Wurttemberg, Germany), 8(20), e2102555-e2102555 (2021-08-17)
DNA-binding proteins, including transcription factors (TFs), play essential roles in various cellular processes and pathogenesis of diseases, deeming to be potential therapeutic targets. However, these proteins are generally considered undruggable as they lack an enzymatic catalytic site or a ligand-binding
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
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
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