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Zastosowanie cyklicznych, 5-członowych odczynników fosforylujących oraz fosfitylujących w chemicznej syntezie biofosforanów

Olesiak M., Okruszek A.

Wiadomości Chemiczne

2009

[Z] 63, 5-6

437-459

Cyclic, 5-membered derivatives of three- and tetracoordinated phosphorus constitute an important group of organophosphorus compounds in light of their increased reactivity towards nucleophilic reagents. This surprising reactivity is caused by steric strain present in 5-membered heterocyclic ring, which is then released on formation of reaction intermediates possessing pentacovalent phosphorus atom. This problem was thoroughly analyzed by Westheimer in his classical paper [13]. The title cyclic compounds found an application in the chemical synthesis of biophosphates such as phospholipid derivatives [15-17, 19-21] or nucleoside phosphates [14, 18], however, in spite of numerous efforts (especially by the groups of Ugi and Ramirez) their applicability to efficient formation of internucleotide linkage was rather limited [22-26]. Further development of this matter was achieved by Stec and coworkers [27], who in 1991 applied appropriately protected P-chiral nucleoside- -3'-O-(2-thiono-1,3,2-oksathiaphospholane)s for the synthesis of stereoregular oligo(nucleoside phosphorothioate)s. In fact, the oxathiaphospholane method was for many years a unique successful approach to stereocontrolled synthesis of phosphorothioate analogs of oligonucleotides. The method was later modified and applied for preparation of other phosphorothioate analogs of nucleotides [29-36], including compounds not containing sulphur [37-39]. Further modification led to so called dithiaphospholane approach, allowing an efficient synthesis of oligo(nucleoside phosphorodithioate)s [40] and other phosphorodithioate analogs of nucleotides [41-44]. An alternative approach to the synthesis of stereoregular oligo(nucleoside phosphorothioate)s, involving an application of P-chiral nucleoside oxazaphospholidine derivatives had at first a limited success (Agrawal et al. [45-47], Beaucage et al. [48]), however, recent achievements of Wada et al. [49] made compounds of this series efficient precursors for stereocontrolled synthesis of phosphorothioate analogs of oligonucleotides.