Nucleoside phosphate analogues of biological interest, and their synthesis via aryl nucleoside H-phosphonates as intermediates
Cieślak, J.; Sobkowski, M.; Jankowska, J.; Wenska, M.; Szymczak, M.; Imiolczyk, B.; Zagórowska, I.; Shugar, D.; Stawiński, J.; Kraszewski, A.
Acta Biochimica Polonica 48(2): 429-442
2001
ISSN/ISBN: 0001-527X PMID: 11732613 Document Number: 526799
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.