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Safety Information

929476

Sigma-Aldrich

N-Acetyl-S-(2-amino-9-(4-fluorobenzyl)-6-oxo-6,9-dihydro-1H-purin-8-yl)-L-cysteine

≥95%

Synonym(s):

p-Fluorobenzylguanine ligand, AUTAC ligand, FBnG

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About This Item

Empirical Formula (Hill Notation):
C17H17FN6O4S
CAS Number:
2241669-86-1
Molecular Weight:
420.42
MDL number:
MFCD32670504
UNSPSC Code:
12352209
NACRES:
NA.21

Quality Level

100

Assay

≥95%

form

powder or chunks

reaction suitability

reagent type: ligand

storage temp.

2-8°C

SMILES string

O=C1NC(N)=NC2=C1N=C(SC[C@@H](C(O)=O)NC(C)=O)N2CC3=CC=C(C=C3)F

Application

N-acetyl-S-(2-amino-9-(4-fluorobenzyl)-6-oxo-6,9-dihydro-1H-purin-8-yl)-L-cysteine is a p-fluorobenzylguanine (FBnG) based ligand used to initiate selective autophagy as a strategy for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology.

Related Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

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Other Notes

AUTACs: Cargo-Specific Degraders Using Selective Autophagy

Iterative Design and Optimization of Initially Inactive Proteolysis Targeting Chimeras (PROTACs) Identify VZ185 as a Potent, Fast, and Selective von Hippel-Lindau (VHL) Based Dual Degrader Probe of BRD9 and BRD7

BAF complex vulnerabilities in cancer demonstrated via structure-based PROTAC design

Cereblon versus VHL: Hijacking E3 ligases against each other using PROTACs

Systematic exploration of different E3 ubiquitin ligases: an approach towards potent and selective CDK6 degraders

Legal Information

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

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

929476-VAR:
929476-250MG:
929476-50MG:
929476-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
0000179622
0000195572

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William Farnaby et al.
Nature chemical biology, 15(7), 672-680 (2019-06-11)
Targeting subunits of BAF/PBAF chromatin remodeling complexes has been proposed as an approach to exploit cancer vulnerabilities. Here, we develop proteolysis targeting chimera (PROTAC) degraders of the BAF ATPase subunits SMARCA2 and SMARCA4 using a bromodomain ligand and recruitment of
Miriam Girardini et al.
Bioorganic & medicinal chemistry, 27(12), 2466-2479 (2019-03-04)
The von Hippel-Lindau (VHL) and cereblon (CRBN) proteins are substrate recognition subunits of two ubiquitously expressed and biologically important Cullin RING E3 ubiquitin ligase complexes. VHL and CRBN are also the two most popular E3 ligases being recruited by bifunctional
Christian Steinebach et al.
Chemical science, 11(13), 3474-3486 (2020-11-03)
Cyclin-dependent kinase 6 (CDK6) is an important regulator of the cell cycle. Together with CDK4, it phosphorylates and inactivates retinoblastoma (Rb) protein. In tumour cells, CDK6 is frequently upregulated and CDK4/6 kinase inhibitors like palbociclib possess high activity in breast
Vittoria Zoppi et al.
Journal of medicinal chemistry, 62(2), 699-726 (2018-12-13)
Developing PROTACs to redirect the ubiquitination activity of E3 ligases and potently degrade a target protein within cells can be a lengthy and unpredictable process, and it remains unclear whether any combination of E3 and target might be productive for
Daiki Takahashi et al.
Molecular cell, 76(5), 797-810 (2019-10-14)
Protein silencing represents an essential tool in biomedical research. Targeted protein degradation (TPD) strategies exemplified by PROTACs are rapidly emerging as modalities in drug discovery. However, the scope of current TPD techniques is limited because many intracellular materials are not

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