Nonglycoside analogs of nucleotides

Conclusions We synthesized nine analogs of dinucleoside monophosphates that contain 9-(2-hydroxyethyl)adenine, 9-(3-hydroxypropyl)adenine, and 9-(4-hydroxybutyl)adenine as the 3 residue, and the natural nucleosides: uridine, cytidine, adenosine, guanosine, and inosine as the 5 residue.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 915–916, April, 1975.     

Nonglycoside analogs of nucleotides

N¹-(2′,3′-Dihydroxypropyl)uracil, -thymine, -cytosine, and N⁹-(2′,3′-dihydroxypropyl)adenine were synthesized by alkylation of nucleic bases with 2,3-O-isopropylideneglycerol chlorohydrin, subsequent separation of the resulting mixtures, and removal of the protective groupings. Phosphorylation of these compounds or of their selectively substituted derivatives gave 2′(3′)-monophosphates, which were converted to 2′,3′-cyclophosphates by reaction with N,N′-dicyclohexylcarbodiimide. Thionation of the corresponding cytosine derivatives gave N¹-(2′,3′-dihydroxypropyl)-4-thiouracil and its 2′(3′) phosphate.     

Synthesis of 4-thiouridine derivatives

The thionation of a protected uridine with the aid of P₂S₅ has given the corresponding 4-thiouridine derivatives, which have been phosphorylated at the 5 or the 2(3)hydroxyl. On being heated in aqueous pyridine solution with liquid hydrogen sulfide, cytidine phosphates also form 4-thiouridine phosphates. 4-Thiouridine 2,3-cyclophosphate has been obtained.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 996–1000, July, 1973.The authors thank M. Ya. Karpeiskii for his constant interest in the work and for valuable critical observations.     

Vitamin b6 analogs

The synthesis of 2- and 5-modified analogs of pyridoxine from which analogs of pyridoxal and pyridoxal 5-phosphate were obtained is described. The transition to analogs of pyridoxamine and pyridoxamine 5-phosphate is realized by hydrogenation of the oximes of these aldehydes.See [1] for communication XV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 655–660, May, 1974.