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917443

Sigma-Aldrich

BocA1V2PF2-NHC6-NH2

Synonym(s):

tert-Butyl ((S)-1-(((S)-2-((S)-2-(((S)-1-((6-aminohexyl)amino)-3-(4-fluorophenyl)-1-oxopropan-2-yl)carbamoyl)pyrrolidin-1-yl)-1-cyclohexyl-2-oxoethyl)amino)-1-oxopropan-2-yl)carbamate, AVP conjugate for IAP-mediated protein degrader development, SNIPER building block

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About This Item

Empirical Formula (Hill Notation):
C36H57FN6O6
Molecular Weight:
688.87
UNSPSC Code:
41116105
NACRES:
NA.22

ligand

BocA1V2PF2

Quality Level

form

powder

reaction suitability

reactivity: carboxyl reactive
reagent type: ligand-linker conjugate

functional group

amine

storage temp.

2-8°C

SMILES string

C[C@H](NC(OC(C)(C)C)=O)C(N[C@H](C(N1CCC[C@H]1C(N[C@H](C(NCCCCCCN)=O)CC2=CC=C(C=C2)F)=O)=O)C3CCCCC3)=O

Application

Protein degrader building block BocA1V2PF2-NHC6-NH2 enables the synthesis of molecules for targeted protein degradation and SNIPER (specific and non-genetic inhibitor of apoptosis protein (IAP)-dependent protein erasers) technology. Developed in partnership with ComInnex, this conjugate contains an in silico-derived IAP-recruiting ligand, an alkyl-chain crosslinker, and a pendant amine for reactivity with an acid on a target warhead. Because even slight alterations in ligands and crosslinkers can affect ternary complex formation between the target, E3 ligase, and protein degrader, many analogs are prepared to screen for optimal target degradation. When used with other protein degrader building blocks with a terminal amine, including CRBN and VHL targeted, parallel synthesis can be used to more quickly generate SNIPER and PROTAC® degrader libraries that feature variation in crosslinker length, composition, and E3 ligase ligand. Learn more about the novel IAP ligands generated through virtual screening of AVP mimetics in our Technology Spotlight.

Building blocks in this series:
916714 BocA1V2PF2
917443 BocA1V2PF2-NHC6-NH2
917699 BocA1V2PF2-NHC10-NH2
917958 BocA1V2PF2-NHPEG1-NH2
916692 BocA1V2PF2-NHPEG3-NH2

Technology Spotlight: Degrader Building Blocks with Inhibitor of Apoptosis Protein (IAP) In Silico-Derived Ligands

Legal Information

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

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Tasuku Ishida et al.
SLAS discovery : advancing life sciences R & D, 26(4), 484-502 (2020-11-05)
Bifunctional degrader molecules, also called proteolysis-targeting chimeras (PROTACs), are a new modality of chemical tools and potential therapeutics to understand and treat human disease. A required PROTAC component is a ligand binding to an E3 ubiquitin ligase, which is then joined to another ligand binding to a protein to
Mikihiko Naito et al.
Drug discovery today. Technologies, 31, 35-42 (2019-06-16)
The induction of protein degradation by chimeric small molecules represented by proteolysis-targeting chimeras (PROTACs) is an emerging approach for novel drug development. We have developed a series of chimeric molecules termed specific and non-genetic inhibitor of apoptosis protein (IAP)-dependent protein
Nobumichi Ohoka et al.
The Journal of biological chemistry, 292(11), 4556-4570 (2017-02-06)
Many diseases, especially cancers, result from aberrant or overexpression of pathogenic proteins. Specific inhibitors against these proteins have shown remarkable therapeutic effects, but these are limited mainly to enzymes. An alternative approach that may have utility in drug development relies

Articles

Targeted protein degradation reduces disease-relevant proteins in cells using small molecules, hijacking endogenous proteolysis systems.

Targeted protein degradation reduces disease-relevant proteins in cells using small molecules, hijacking endogenous proteolysis systems.

Targeted protein degradation reduces disease-relevant proteins in cells using small molecules, hijacking endogenous proteolysis systems.

Targeted protein degradation reduces disease-relevant proteins in cells using small molecules, hijacking endogenous proteolysis systems.

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