Nucleoside phosphate analogues of biological interest, and their synthesis via aryl nucleoside H-phosphonates as intermediates.
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.
Cieślak
J
J
Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznań.
Sobkowski
M
M
Jankowska
J
J
Wenska
M
M
Szymczak
M
M
Imiolczyk
B
B
Zagórowska
I
I
Shugar
D
D
Stawiński
J
J
Kraszewski
A
A
D002384:Catalysis; D004951:Esterification; D008722:Methods; D015394:Molecular Structure; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry
D009711:Nucleotides; D010710:Phosphates; C035638:thiophosphoric acid