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916870

Sigma-Aldrich

4-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzoic acid

≥95%

Synonym(s):

Semi-flexible linker for PROTAC® development

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About This Item

Empirical Formula (Hill Notation):
C17H23NO4
CAS Number:
149353-75-3
Molecular Weight:
305.37
MDL number:
MFCD02178897
UNSPSC Code:
12352106

Quality Level

100

Assay

≥95%

form

powder

reaction suitability

reagent type: linker

functional group

Boc
carboxylic acid

storage temp.

2-8°C

SMILES string

O=C(N(CC1)CCC1C(C=C2)=CC=C2C(O)=O)OC(C)(C)C

InChI

1S/C17H23NO4/c1-17(2,3)22-16(21)18-10-8-13(9-11-18)12-4-6-14(7-5-12)15(19)20/h4-7,13H,8-11H2,1-3H3,(H,19,20)

InChI key

YCNVQGGUCDVTIZ-UHFFFAOYSA-N

Application

4-(1-(tert-Butoxycarbonyl)piperidin-4-yl)benzoic acid is a 4-aryl piperidine useful as a semi-flexible linker in PROTAC development for targeted protein degradation. Incorporation of rigidity into the linker region of bifunctional protein degraders may impact the 3D orientation of the degrader and thus ternary complex formation as well as optimization of drug-like properties.

Other Notes

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Crosslinkers for Bioconjugation

Portal: Building PROTAC® Degraders for Targeted Protein Degradation

Legal Information

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

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Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H315,H317,H319,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV9412

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Andrei A Krysko et al.
Bioorganic & medicinal chemistry letters, 21(19), 5971-5974 (2011-08-20)
The novel RGD mimetics with phthalimidine central fragment were synthesized with the use of 4-piperidine-4-yl-butyric, 4-piperidine-4-yl-benzoic, 4-piperazine-4-yl-benzoic and 1,2,3,4-tetrahydroisoquinoline-7-carboxylic acids as surrogates of Arg motif. The synthesized compounds potently inhibited platelet aggregation in vitro and blocked FITC-Fg binding to α(IIb)β(3)
Andrei A Krysko et al.
Bioorganic & medicinal chemistry letters, 26(7), 1839-1843 (2016-02-26)
A series of 2-piperazin-1-yl-quinazolines were synthesized and evaluated for their antiaggregative activity. The synthesized small molecule compounds have potently inhibited platelet aggregation in vitro and blocked FITC-Fg binding to αIIbβ3 integrin in a suspension of washed human platelets. The key
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A new catalytic manifold that merges photoredox with nickel catalysis in aqueous solution is presented. Specifically, the combination of a highly active, yet air-stable, nickel precatalyst with a new electron-deficient pyridyl carboxamidine ligand was key to the development of a
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