Nonglycoside analogs of nucleotides |
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Authors: | A M Kritsyn L I Kolobushkina S N Mikhailov V L Florent'ev |
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Institution: | 1. Institute of Molecular Biology, Academy of Sciences of the USSR, Moscow
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Abstract: | 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. |
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