Overview of the synthesis of nucleoside phosphates and polyphosphates.
This overview summarizes methodology used for the synthesis of nucleoside mono-, di-, and triphosphates. Selected techniques such as the Mitsunobu reaction, displacement reactions involving nucleoside 5'-tosylates, "anion-exchange" techniques, and phosphoramidite and phosphoramidate methodologies are highlighted. The chemistry of phosphorylation is detailed with respect to advantages and limitations under various conditions. Applicability of the methods toward the synthesis of analogs such as imidophosphates, phosphorothioates, and radiolabeled nucleotides is also addressed.
Johnson
David C
DC
Indiana University, Bloomington, Indiana, USA.
Widlanski
Theodore S
TS
D000577:Amides / Q000737:chemistry; D000812:Anhydrides / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D008954:Models, Biological; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D009711:Nucleotides / Q000737:chemistry; D009841:Oligonucleotides / Q000138:chemical synthesis; D063065:Organophosphonates / Q000737:chemistry; D010710:Phosphates / Q000138:chemical synthesis; D010724:Phosphoadenosine Phosphosulfate / Q000138:chemical synthesis / Q000737:chemistry; D010756:Phosphoric Acids / Q000737:chemistry / Q000494:pharmacology; D010758:Phosphorus / Q000737:chemistry; D010766:Phosphorylation; D011122:Polyphosphates / Q000138:chemical synthesis*
D000577:Amides; D000812:Anhydrides; D009705:Nucleosides; D009711:Nucleotides; D009841:Oligonucleotides; D063065:Organophosphonates; D010710:Phosphates; D010756:Phosphoric Acids; D011122:Polyphosphates; D010758:Phosphorus; C010288:phosphorochloridic acid; D010724:Phosphoadenosine Phosphosulfate; C011067:phosphoramidic acid