title: Incorporation of arginine mimetic residue into peptides for recognition of double stranded nucleic acid structure: Binding and aggregation studies.
abstract: An arginine mimetic, featuring a guanidiniocarbonypyrrol as artificial anion binding site (GCP), was introduced into short peptides to study their binding and aggregation with double stranded DNA and RNA. While the incorporation of this GCP modification did not significantly change the overall binding affinity for DNA/RNA, their interactions were more sensitive with respect to the type of polynucleotides. Peptide 4, with four GCP modifications, exhibited amazing fluorescent selectivity for AU- and (to a lesser extent) AT- sequences. GC-containing DNA showed much lower response. Additionally, exclusively tri-GCP modified peptide 3 showed intriguing exciton-coupled bisignate ICD bands for all studied DNA/RNA which suggested that a well-defined GCP-dimer bound into DNA/RNA groove..
authors.affiliation: Institute for Organic Chemistry, University of Duisburg-Essen, 45117 Essen, Germany.
authors.forename: Mao
authors.initials: M
authors.lastname: Li
authors.affiliation: Division of Organic Chemistry & Biochemistry, Ruđer Bošković Institute, P.O. Box 180, 10002 Zagreb, Croatia.
authors.forename: Marija
authors.initials: M
authors.lastname: Matković
authors.affiliation: Division of Organic Chemistry & Biochemistry, Ruđer Bošković Institute, P.O. Box 180, 10002 Zagreb, Croatia.
authors.forename: Ivo
authors.initials: I
authors.lastname: Piantanida
authors.affiliation: Institute for Organic Chemistry, University of Duisburg-Essen, 45117 Essen, Germany. Electronic address: carsten.schmuck@uni-due.de.
authors.forename: Carsten
authors.initials: C
authors.lastname: Schmuck
mesh_terms: D001120:Arginine / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000737:chemistry*; D018716:Molecular Mimicry; D009691:Nucleic Acid Denaturation; D010455:Peptides / Q000737:chemistry*; D012330:RNA, Double-Stranded / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013057:Spectrum Analysis / Q000379:methods
chemical_list: D010455:Peptides; D012330:RNA, Double-Stranded; D004247:DNA; D001120:Arginine
keywords: Arginine mimic; DNA/RNA recognition; Hydrogen bonds; Ion pair; Polynucleotide binding