S-&thy1 thymidine (SP)-3',5'-cyclic phosphorothioate and S-methyl 5'-O+hyaudyl 3'thymidyl (Rp)-phosphorothioate are readily converted by means of sodium ["Ol-hydroxide into the corresponding ["Ol-phosphate diesters stereospecifically with retention of configuration at phosphorus.
Stereospecific conversion of P-chiral nucleoside phosphorothioates into [18O]phosphates
β Scribed by Piotr Guga; Andrzej Okruszek
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 210 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
P-chiral phosphorothioate analogs of thymidine and adenosine nucleotides are transformed in high yield with retention of configuration by [180]chloral and [l80]styrene oxide into corresponding nucleoside [l*O]phosphates. It has been shown in our recent reports that 18 0-labelled reagents such as dimethyl sulphoxide (1) ', styrene oxide (2-j 2 and chloral (z)3 may be successfully applied for a stereospecific conversion of P-chiral cyclic dialkyl phosphorothioates into corresponding 4 [l'O]phosphates
π SIMILAR VOLUMES
Czs-and trans-2-hydroxy-2-thlono-4-methyl-1,3,2-dloxaphosphorlnanes are cleanly transformed by means of [180]-DMSO Into corresponding 2-(['80]-oxo)-derivatives with ca 90% znuerszon of conflguratlon at phosphorus atom.
Sunmary: "0 NMR spectra of the title compounds show well-separated P=O" peaks and configurationally diagnostic 6"O values and line widths. Use of these features to assign configurational purity to ("0, "0) P-chiral nucleoside monophosphate diesters is proposed. Solvent CD3CN CD3CN CD3CN CD3CN CD3CN