title: Straightforward Synthesis of Purine 4'-Alkoxy-2'-deoxynucleosides: First Report of Mixed Purine-Pyrimidine 4'-Alkoxyoligodeoxynucleotides as New RNA Mimics.
abstract: Purine and pyrimidine 4'-alkoxy-2'-deoxynucleosides were efficiently prepared from nucleoside 4'-5'-enol acetates in three steps by N-iodosuccinimide promoted alkoxylation, hydrolysis, and reduction followed by conversion to phosphoramidite monomers for the solid-phase synthesis of the oligonucleotides. Fully modified 4'-alkoxyoligodeoxynucleotides, which are characterized by a prevalent N-type (RNA-like) conformation, exhibited superior chemical and nuclease resistance as well as excellent hybridization properties with a strong tendency for RNA-selective hybridization, suggesting a potential application of 4'-alkoxy-oligodeoxynucleotides in antisense technologies.
authors.affiliation: Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic v.v.i., Flemingovo nám. 2, 166 10 Praha 6, Czech Republic.
authors.forename: Magdalena
authors.initials: M
authors.lastname: Petrová
authors.affiliation: Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic v.v.i., Flemingovo nám. 2, 166 10 Praha 6, Czech Republic.
authors.forename: Ondřej
authors.initials: O
authors.lastname: Páv
authors.affiliation: Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic v.v.i., Flemingovo nám. 2, 166 10 Praha 6, Czech Republic.
authors.forename: Miloš
authors.initials: M
authors.lastname: Buděšínský
authors.affiliation: Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic v.v.i., Flemingovo nám. 2, 166 10 Praha 6, Czech Republic.
authors.forename: Eva
authors.initials: E
authors.lastname: Zborníková
authors.affiliation: Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic v.v.i., Flemingovo nám. 2, 166 10 Praha 6, Czech Republic.
authors.forename: Pavel
authors.initials: P
authors.lastname: Novák
authors.affiliation: Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic v.v.i., Flemingovo nám. 2, 166 10 Praha 6, Czech Republic.
authors.forename: Šárka
authors.initials: Š
authors.lastname: Rosenbergová
authors.affiliation: Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic v.v.i., Flemingovo nám. 2, 166 10 Praha 6, Czech Republic.
authors.forename: Ondřej
authors.initials: O
authors.lastname: Pačes
authors.affiliation: Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic v.v.i., Flemingovo nám. 2, 166 10 Praha 6, Czech Republic.
authors.forename: Radek
authors.initials: R
authors.lastname: Liboska
authors.affiliation: Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic v.v.i., Flemingovo nám. 2, 166 10 Praha 6, Czech Republic.
authors.forename: Ivana
authors.initials: I
authors.lastname: Dvořáková
authors.affiliation: Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic v.v.i., Flemingovo nám. 2, 166 10 Praha 6, Czech Republic.
authors.forename: Ondřej
authors.initials: O
authors.lastname: Šimák
authors.affiliation: Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic v.v.i., Flemingovo nám. 2, 166 10 Praha 6, Czech Republic.
authors.forename: Ivan
authors.initials: I
authors.lastname: Rosenberg
mesh_terms: D008968:Molecular Conformation; D015394:Molecular Structure; D009690:Nucleic Acid Conformation; D009693:Nucleic Acid Hybridization; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D016376:Oligonucleotides, Antisense / Q000737:chemistry*; D011687:Purines / Q000737:chemistry*; D012313:RNA / Q000737:chemistry*; D013388:Succinimides / Q000737:chemistry
chemical_list: D009838:Oligodeoxyribonucleotides; D016376:Oligonucleotides, Antisense; D011687:Purines; D013388:Succinimides; C008155:N-iodosuccinimide; D012313:RNA; C030985:purine