Synthesis and structure of 1,4-dipiperazino benzenes: chiral terphenyl-type peptide helix mimetics.
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.
Maity
Prantik
P
Institut für Organische Chemie, Universität Regensburg, D-93040 Regensburg, Germany.
König
Burkhard
B
D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D018716:Molecular Mimicry; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D017433:Protein Structure, Secondary; D013730:Terphenyl Compounds / Q000737:chemistry*
D001555:Benzene Derivatives; D010455:Peptides; D013730:Terphenyl Compounds