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Triostin a derived cyclopeptide as architectural template for the alignment of four recognition units.

Kotyrba UM, Pröpper K, Sachs EF, Myanovska A, Joppe T, Lissy F, Sheldrick GM, Koszinowski K, Diederichsen U - ChemistryOpen (2014)

Bottom Line: 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.The new tetra-nucleobase binders are synthesized as aza-TANDEM derivatives lacking the N-methylation of triostin A and based on a cyclopeptide backbone.

View Article: PubMed Central - PubMed

Affiliation: Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen Tammannstrasse 2, 37077 Göttingen (Germany) E-mail: udieder@gwdg.de.

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.

No MeSH data available.


Related in: MedlinePlus

Mass spectrum of mass-selected (22+3NH4)3+ and its fragment ions produced upon collision-induced dissociation.
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fig07: Mass spectrum of mass-selected (22+3NH4)3+ and its fragment ions produced upon collision-induced dissociation.

Mentions: Whereas no ions with significant intensity were observed for m/z>1300, additional ions were found at m/z 858–867 (see Supporting Information). From their exact m/z ratios and their characteristic isotope patterns displaying spacings of 0.33 amu, these ions were identified as dimers of 2, which acquire a triple charge by binding three H+, NH4+, and/or Na+ ions. This assignment was further supported by collision-induced dissociation (CID) experiments, which showed these dimers to dissociate into singly and doubly charged monomers by Coulomb explosion (e.g., (22+3NH4)3+→(2+2NH4)2++(2+NH4)+, Figure 7).15


Triostin a derived cyclopeptide as architectural template for the alignment of four recognition units.

Kotyrba UM, Pröpper K, Sachs EF, Myanovska A, Joppe T, Lissy F, Sheldrick GM, Koszinowski K, Diederichsen U - ChemistryOpen (2014)

Mass spectrum of mass-selected (22+3NH4)3+ and its fragment ions produced upon collision-induced dissociation.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4232271&req=5

fig07: Mass spectrum of mass-selected (22+3NH4)3+ and its fragment ions produced upon collision-induced dissociation.
Mentions: Whereas no ions with significant intensity were observed for m/z>1300, additional ions were found at m/z 858–867 (see Supporting Information). From their exact m/z ratios and their characteristic isotope patterns displaying spacings of 0.33 amu, these ions were identified as dimers of 2, which acquire a triple charge by binding three H+, NH4+, and/or Na+ ions. This assignment was further supported by collision-induced dissociation (CID) experiments, which showed these dimers to dissociate into singly and doubly charged monomers by Coulomb explosion (e.g., (22+3NH4)3+→(2+2NH4)2++(2+NH4)+, Figure 7).15

Bottom Line: 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.The new tetra-nucleobase binders are synthesized as aza-TANDEM derivatives lacking the N-methylation of triostin A and based on a cyclopeptide backbone.

View Article: PubMed Central - PubMed

Affiliation: Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen Tammannstrasse 2, 37077 Göttingen (Germany) E-mail: udieder@gwdg.de.

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.

No MeSH data available.


Related in: MedlinePlus