title: Triostin a derived cyclopeptide as architectural template for the alignment of four recognition units.
abstract: The DNA bisintercalator triostin A is structurally based on a disulfide-bridged depsipeptide scaffold that provides preorganization of two quinoxaline units in 10.5 Å distance. Triostin A analogues are synthesized with nucleobase recognition units replacing the quinoxalines and containing two additional recognition units in between. Thus, four nucleobase recognition units are organized on a rigid template, well suited for DNA double strand interactions. The new tetra-nucleobase binders are synthesized as aza-TANDEM derivatives lacking the N-methylation of triostin A and based on a cyclopeptide backbone. Synthesis of two tetra-nucleobase aza-TANDEM derivatives is established, DNA interaction analyzed by microscale thermophoresis, cytotoxic activity studied and a nucleobase sequence dependent self-aggregation investigated by mass spectrometry.
authors.affiliation: Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen Tammannstrasse 2, 37077 Göttingen (Germany) E-mail: udieder@gwdg.de.
authors.forename: Ursula M
authors.initials: UM
authors.lastname: Kotyrba
authors.affiliation: Institute of Inorganic Chemistry, Georg-August-University Göttingen Tammannstrasse 4, 37077 Göttingen (Germany).
authors.forename: Kevin
authors.initials: K
authors.lastname: Pröpper
authors.affiliation: Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen Tammannstrasse 2, 37077 Göttingen (Germany) E-mail: udieder@gwdg.de.
authors.forename: Eike-F
authors.initials: EF
authors.lastname: Sachs
authors.affiliation: Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen Tammannstrasse 2, 37077 Göttingen (Germany) E-mail: udieder@gwdg.de.
authors.forename: Anastasiya
authors.initials: A
authors.lastname: Myanovska
authors.affiliation: Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen Tammannstrasse 2, 37077 Göttingen (Germany) E-mail: udieder@gwdg.de.
authors.forename: Tobias
authors.initials: T
authors.lastname: Joppe
authors.affiliation: Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen Tammannstrasse 2, 37077 Göttingen (Germany) E-mail: udieder@gwdg.de.
authors.forename: Friederike
authors.initials: F
authors.lastname: Lissy
authors.affiliation: Institute of Inorganic Chemistry, Georg-August-University Göttingen Tammannstrasse 4, 37077 Göttingen (Germany).
authors.forename: George M
authors.initials: GM
authors.lastname: Sheldrick
authors.affiliation: Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen Tammannstrasse 2, 37077 Göttingen (Germany) E-mail: udieder@gwdg.de.
authors.forename: Konrad
authors.initials: K
authors.lastname: Koszinowski
authors.affiliation: Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen Tammannstrasse 2, 37077 Göttingen (Germany) E-mail: udieder@gwdg.de.
authors.forename: Ulf
authors.initials: U
authors.lastname: Diederichsen
keywords: ESI mass spectrometry; microscale thermophoreses; nucleobase recognition; peptide nucleic acids; structure characterization of biomolecules; triostin A