title: DNA-Templated Synthesis of Perylenediimide Stacks Utilizing Abasic Sites as Binding Pockets and Reactive Sites.
abstract: DNA is considered to be a promising biomolecule as a template and scaffold for arranging and organizing functional molecules on the nanoscale. The construction and evaluation of DNAs containing multiple functional molecules that are useful for optoelectronic devices and sensors has been studied. In this paper we report the efficient incorporation of perylenediimide (PDI) units into DNA by using abasic sites both as binding sites and as reactive sites and the construction of PDI stacks within the DNA structure, accomplished through the preorganization of the PDI units in the hydrophobic pocket within the DNA. Our approach could become a valuable method for construction of DNA/chromophore hybrid structures potentially useful for the design of DNA-based devices and biosensors.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo, 671-2280, Japan.
authors.forename: Tadao
authors.initials: T
authors.lastname: Takada
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo, 671-2280, Japan.
authors.forename: Misa
authors.initials: M
authors.lastname: Ido
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo, 671-2280, Japan.
authors.forename: Akane
authors.initials: A
authors.lastname: Ashida
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo, 671-2280, Japan.
authors.forename: Mitsunobu
authors.initials: M
authors.lastname: Nakamura
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo, 671-2280, Japan.
authors.forename: Kazushige
authors.initials: K
authors.lastname: Yamana
mesh_terms: D001665:Binding Sites; D015374:Biosensing Techniques; D004247:DNA / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D007094:Imides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010569:Perylene / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D007094:Imides; C521332:perylenediimide; D010569:Perylene; D004247:DNA
keywords: DNA; abasic sites; bioconjugation; reductive amination; stacking interactions