title: Probing the shielding properties of aptameric protective groups.
abstract: Site-specific derivatization of chemically equivalent functional groups has recently been facilitated by the introduction of high-affinity aptamers as non-covalent protective groups. More specifically, a series of RNA aptamers have proven to be highly efficient in enhancing the regioselectivity of reactions with the aminoglycoside antibiotic neomycin B, which carries several chemically indistinguishable amino and hydroxy groups. Since small-molecule targets tend to exhibit multiple modes of binding with a single aptamer, the impact of secondary binding sites on the regioselectivity should be considered. To address this issue, we investigated a series of well-characterized RNA aptamers that bind neomycin B and propose a mechanism that accounts for the regioselective outcome of these transformations. We further demonstrate that the regioselectivity induced by non-covalent aptamer protective groups is determined by the number of binding sites, their affinity, and the mode of interaction with the guest molecule.
authors: Department of Polymer Chemistry, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, Groningen, 9747 AG Groningen (The Netherlands).
authors: Andreas A
authors: AA
authors: Bastian
authors: Alberto
authors: A
authors: Rodríguez-Pulido
authors: Agnieszka
authors: A
authors: Gruszka
authors: Jennifer Y
authors: JY
authors: Gerasimov
authors: Andreas
authors: A
authors: Herrmann
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry; D052157:Aptamers, Nucleotide / Q000737:chemistry*; D001483:Base Sequence; D001665:Binding Sites; D005601:Framycetin / Q000737:chemistry; D066244:Proton Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000900:Anti-Bacterial Agents; D052157:Aptamers, Nucleotide; D005601:Framycetin
keywords: RNA; aminoglycosides; aptameric protective groups; aptamers; regioselectivity