Synthesis and structure of 1,4-dipiperazino benzenes: Chiral terphenyl-type peptide helix mimetics

Maity, Prantik and Koenig, Burkhard (2008) Synthesis and structure of 1,4-dipiperazino benzenes: Chiral terphenyl-type peptide helix mimetics. ORGANIC LETTERS, 10 (7). pp. 1473-1476. ISSN 1523-7060, 1523-7052

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Abstract

The terphenyl structure has been proven to be an ideal scaffold mimicking side-chain functionalities of peptidic alpha-helices. The synthesis of 1,4-dipiperazino benzenes, using stepwise transition metal-catalyzed N-arylation of chiral piperazines to a central benzene core is reported. The structure determination by X-ray crystallography reveals a geometrical arrangement of the hydrophobic side chains resembling the orientation of key i, i + 3, and i + 7 positions in a peptidic alpha-helix or in terphenyl helix mimetics.

Item Type: Article
Uncontrolled Keywords: PALLADIUM-CATALYZED AMINATION; PROTEIN-PROTEIN INTERACTIONS; NITROGEN BOND FORMATION; ALPHA-HELIX; ARYL HALIDES; SECONDARY STRUCTURE; ROOM-TEMPERATURE; AROMATIC AMINATION; COUPLING REACTIONS; AMINES;
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Dr. Gernot Deinzer
Date Deposited: 04 Nov 2020 10:00
Last Modified: 04 Nov 2020 10:00
URI: https://pred.uni-regensburg.de/id/eprint/31060

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