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917206

Sigma-Aldrich

A1V2PF1-NHEt-C10-NH2

Synonym(s):

(S)-1-((S)-2-((S)-2-((10-Aminodecyl)amino)propanamido)-2-cyclohexylacetyl)-N-((S)-1-(ethylamino)-1-oxo-3-phenylpropan-2-yl)pyrrolidine-2-carboxamide, AVP conjugate for IAP-mediated protein degrader development, SNIPER building block

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About This Item

Empirical Formula (Hill Notation):
C37H62N6O4
Molecular Weight:
654.93
UNSPSC Code:
41116105
NACRES:
NA.22

ligand

A1V2PF1

Quality Level

100

form

crystals

reaction suitability

reactivity: carboxyl reactive
reagent type: ligand-linker conjugate

functional group

amine

storage temp.

2-8°C

SMILES string

C[C@H](NCCCCCCCCCCN)C(N[C@H](C(N1CCC[C@H]1C(N[C@H](C(NCC)=O)CC2=CC=C(C=C2)F)=O)=O)C3CCCCC3)=O

Application

Protein degrader building block A1V2PF1-NHEt-C10-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:
917222 A1V2PF1-NHEt
916943 A1V2PF1-NHEt-C6-NH2
917206 A1V2PF1-NHEt-C10-NH2
917451 A1V2PF1-NHEt-PEG1-NH2
917702 A1V2PF1-NHEt-PEG3-NH2

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

Other Notes

In Vivo Knockdown of Pathogenic Proteins via Specific and Nongenetic Inhibitor of Apoptosis Protein (IAP)-dependent Protein Erasers (SNIPERs)

SNIPERs−Hijacking IAP activity to induce protein degradation

E3 Ligase Ligands for PROTACs: How They Were Found and How to Discover New Ones

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

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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

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.

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