title: Nucleoside phosphate analogues of biological interest, and their synthesis via aryl nucleoside H-phosphonates as intermediates.
abstract: This review presents a brief account of the chemistry and mechanistic aspects of aryl H-phosphonates, and selected applications of this class of compounds as intermediates in the synthesis of a wide range of biologically important analogues of nucleoside phosphates, and oligonucleotides, in which the phosphate moieties are replaced by other structurally related groups. The aryl nucleoside H-phosphonates, compounds of controlled reactivity, have proven to be more versatile and superior to various mixed anhydrides as synthetic intermediates, particularly for preparation of nucleotide analogues bearing P-N or P-S bonds in various configurational arrangements at the phosphate moiety.
authors.affiliation: Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznań.
authors.forename: J
authors.initials: J
authors.lastname: Cieślak
authors.forename: M
authors.initials: M
authors.lastname: Sobkowski
authors.forename: J
authors.initials: J
authors.lastname: Jankowska
authors.forename: M
authors.initials: M
authors.lastname: Wenska
authors.forename: M
authors.initials: M
authors.lastname: Szymczak
authors.forename: B
authors.initials: B
authors.lastname: Imiolczyk
authors.forename: I
authors.initials: I
authors.lastname: Zagórowska
authors.forename: D
authors.initials: D
authors.lastname: Shugar
authors.forename: J
authors.initials: J
authors.lastname: Stawiński
authors.forename: A
authors.initials: A
authors.lastname: Kraszewski
mesh_terms: D002384:Catalysis; D004951:Esterification; D008722:Methods; D015394:Molecular Structure; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry
chemical_list: D009711:Nucleotides; D010710:Phosphates; C035638:thiophosphoric acid