title: Enzymatic resolution and base pairing properties of D- and L-cyclohexenyl nucleic acids (CeNA).
abstract: An enzymatic transesterification reaction afforded large scale resolution of the cyclohexenol precursor needed for preparation of both series of CeNA building blocks. CeNA oligos of "D-like" chirality display a strong and selective interaction with RNA, while preserving RNase H activity, and therefore have potential as antisense constructs. CeNAs of opposite chirality form a self-pairing system on their own.
authors.affiliation: Laboratory for Medicinal Chemistry, Rega Institute for Medical Research, Leuven, Belgium.
authors.forename: Ping
authors.initials: P
authors.lastname: Gu
authors.forename: Guy
authors.initials: G
authors.lastname: Schepers
authors.forename: Carsten
authors.initials: C
authors.lastname: Griebel
authors.forename: Jef
authors.initials: J
authors.lastname: Rozenski
authors.forename: Hans-Joachim
authors.initials: HJ
authors.lastname: Gais
authors.forename: Piet
authors.initials: P
authors.lastname: Herdewijn
authors.forename: Arthur
authors.initials: A
authors.lastname: Van Aerschot
mesh_terms: D020137:Base Pair Mismatch; D020029:Base Pairing; D004247:DNA / Q000737:chemistry; D006868:Hydrolysis; D008956:Models, Chemical; D009690:Nucleic Acid Conformation; D009692:Nucleic Acid Heteroduplexes / Q000737:chemistry; D009693:Nucleic Acid Hybridization; D009696:Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry; D016376:Oligonucleotides, Antisense / Q000737:chemistry; D012313:RNA / Q000737:chemistry; D016914:Ribonuclease H / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D009692:Nucleic Acid Heteroduplexes; D009696:Nucleic Acids; D009841:Oligonucleotides; D016376:Oligonucleotides, Antisense; D012313:RNA; D004247:DNA; D016914:Ribonuclease H