title: Nucleosides with Transposed Base or 4'-Hydroxymethyl Moieties and Their Corresponding Oligonucleotides.
abstract: This review focuses on 4'-hydroxymethyl- or nucleobase-transposed nucleosides, nucleotides, and nucleoside phosphonates, their stereoisomers, and their close analogues. The biological activities of all known 4'-hydroxymethyl- or nucleobase-transposed nucleosides, nucleotides, and nucleoside phosphonates as potential antiviral or anticancer agents are compiled. The routes that have been taken for the chemical synthesis of such nucleoside derivatives are described, with special attention to the innovative strategies. The enzymatic synthesis, base-pairing properties, structure, and stability of oligonucleotides containing nucleobase- or 4'-hydroxymethyl-transposed nucleotides are discussed. The use of oligonucleotides containing nucleobase- or 4'-hydroxymethyl-transposed nucleotides as small oligonucleotide (e.g., human immunodeficiency virus integrase) inhibitors, in applications such as antisense therapy, silencing RNA (siRNA), or aptamer selections, is detailed.
authors.affiliation: Laboratory for Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Ghent University , Ottergemsesteenweg 460, 9000 Ghent, Belgium.
authors.forename: Kiran
authors.initials: K
authors.lastname: Toti
authors.affiliation: Laboratory for Medicinal Chemistry, Rega Institute for Medical Research, Katholieke Universiteit Leuven , Minderbroedersstraat 10, 3000 Leuven, Belgium.
authors.forename: Marleen
authors.initials: M
authors.lastname: Renders
authors.affiliation: Laboratory for Medicinal Chemistry, Rega Institute for Medical Research, Katholieke Universiteit Leuven , Minderbroedersstraat 10, 3000 Leuven, Belgium.
authors.forename: Elisabetta
authors.initials: E
authors.lastname: Groaz
authors.affiliation: Laboratory for Medicinal Chemistry, Rega Institute for Medical Research, Katholieke Universiteit Leuven , Minderbroedersstraat 10, 3000 Leuven, Belgium.
authors.forename: Piet
authors.initials: P
authors.lastname: Herdewijn
authors.affiliation: Laboratory for Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Ghent University , Ottergemsesteenweg 460, 9000 Ghent, Belgium.
authors.forename: Serge
authors.initials: S
authors.lastname: Van Calenbergh
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry*; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D000998:Antiviral Agents; D009705:Nucleosides; D009841:Oligonucleotides