title: Toward an artificial oxidative DNA photolyase.
abstract: The design, synthesis, structure, and binding affinity of two dioptic receptors for the selective molecular recognition of the cis,syn cyclobutane pyrimidine dimer are reported. The design is based on two 2,6-di(acetamino)pyridine recognition units that are covalently linked via triple bonds to an anthraquinone functional spacer unit. The convergent synthesis uses a modified Sonogashira reaction involving a zinc transmetalation as the key step. The crystal structure of one of the receptors reveals a supramolecular 1D polymer with strong interactions mediated by shape self-complementarity, pi-stacking, and hydrogen bonding between adjacent molecules. Hydrogen bonding between adjacent strands enforces a parallel orientation, which leads to a noncentrosymmetric crystal structure of the highly polar compound. The receptor has an association constant of K(a) = 1.0 x 10(3) M(-1) with the cis,syn pyrimidine dimer, whereas binding of the trans,syn isomer is approximately 1 order of magnitude weaker.
authors.affiliation: Department of Chemistry & Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556-5670, USA.
authors.forename: Mickaël
authors.initials: M
authors.lastname: Pauvert
authors.forename: Patrick
authors.initials: P
authors.lastname: Laine
authors.forename: Marco
authors.initials: M
authors.lastname: Jonas
authors.forename: Olaf
authors.initials: O
authors.lastname: Wiest
mesh_terms: D018360:Crystallography, X-Ray; D004255:Deoxyribodipyrimidine Photo-Lyase / Q000737:chemistry / Q000378:metabolism*; D018384:Oxidative Stress; D011485:Protein Binding
chemical_list: D004255:Deoxyribodipyrimidine Photo-Lyase