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1 Acta Biochimica Polonica

1 2001

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Nucleoside phosphate analogues of biological interest, and their synthesis via aryl nucleoside H-phosphonates as intermediates.

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Cieślak J. , Sobkowski M. , Jankowska J. , Wenska M. , Szymczak M. , Imiołczyk B. , Zagórowska I. , Shugar D. , Stawiński J. , Kraszewski A.

tom 48

nr 2

429-442

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.