title: 1',5'-Anhydro-L-ribo-hexitol Adenine Nucleic Acids (α-L-HNA-A): Synthesis and Chiral Selection Properties in the Mirror Image World.
abstract: The synthesis and a preliminary investigation of the base pairing properties of (6' → 4')-linked 1',5'-anhydro-L-ribo-hexitol nucleic acids (α-L-HNA) have herein been reported through the study of a model oligoadenylate system in the mirror image world. Despite its considerable preorganization due to the rigidity of the "all equatorial" pyranyl sugar backbone, α-L-HNA represents a versatile informational biopolymer, in view of its capability to cross-communicate with natural and unnatural complements in both enantiomeric forms. This seems the result of an inherent flexibility of the oligonucleotide system, as witnessed by the singular formation of iso- and heterochiral associations composed of regular, enantiomorphic helical structures. The peculiar properties of α-L-HNA (and most generally of the α-HNA system) provide new elements in our understanding of the structural prerequisites ruling the stereoselectivity of the hybridization processes of nucleic acids.
authors: †Dipartimento di Scienze Chimiche, Università degli Studi di Napoli Federico II, via Cintia 21, 80126 Napoli, Italy.
authors: Daniele
authors: D
authors: D'Alonzo
authors: ‡Laboratory for Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium.
authors: Mathy
authors: M
authors: Froeyen
authors: ‡Laboratory for Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium.
authors: Guy
authors: G
authors: Schepers
authors: †Dipartimento di Scienze Chimiche, Università degli Studi di Napoli Federico II, via Cintia 21, 80126 Napoli, Italy.
authors: Giovanni
authors: G
authors: Di Fabio
authors: ‡Laboratory for Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium.
authors: Arthur
authors: A
authors: Van Aerschot
authors: ‡Laboratory for Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium.
authors: Piet
authors: P
authors: Herdewijn
authors: †Dipartimento di Scienze Chimiche, Università degli Studi di Napoli Federico II, via Cintia 21, 80126 Napoli, Italy.
authors: Giovanni
authors: G
authors: Palumbo
authors: †Dipartimento di Scienze Chimiche, Università degli Studi di Napoli Federico II, via Cintia 21, 80126 Napoli, Italy.
authors: Annalisa
authors: A
authors: Guaragna
mesh_terms: D000225:Adenine / Q000138:chemical synthesis* / Q000737:chemistry; D020029:Base Pairing; D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D009696:Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D012313:RNA / Q000737:chemistry; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009696:Nucleic Acids; D009841:Oligonucleotides; D013402:Sugar Alcohols; C543192:hexitol; D012313:RNA; D000225:Adenine