Author:
Azhayev Alexei V.,Krayevsky Alexander A.,Smrt Jiří
Abstract
Cytidine 5'-phosphate (Ia) reacts with 1,1'-carbonyldiimidazole under the formation of 2',3'-O-carbonylcytidine 5'-phosphorimidazolidate (IIa) which affords (by the action of 3'-amino-3'-deoxyadenosine (IIIa)) 3'-deoxyadenosine-3'-amidophosphoryl-(3' → 5')-cytidine (IVa) and (by the action of 3'-amino-3-deoxy-N6-dimethyladenosine (IIIc)) 3'-deoxy-N6-dimethyladenosine-3'-amidophosphoryl-(3' → 5')-cytidine (IVc). Starting from adenosine 5'-phosphate (Ib) and 3'-amino-3'-deoxycytidine (IIIb) or the substance IIIc, 3'-deoxycytidine-3'-amidophosphoryl-(3' → 5')-adenosine (IVb) or 3'-deoxy-N6-dimethyladenosine-3'-amidophosphoryl-(3' → 5')-adenosine (IVd) were prepared. 6-Azauridine (V) was transformed, by the action of triphenylphosphine, lithium azide and carbon tetrabromide, followed by the action of triphenylphosphine and ammonia, to 5'-amino-5'-deoxy-6-azauridine (VI). The substance VI was transformed by the action of 2',3'-O-carbonyl-adenosine 5'-phosphorimidazolidate (IIb), to adenylyl-(5' → 5')-5'-amino-5'-deoxy-6-azauridine (VII). The compound IVb is not degraded by snake venom and spleen phosphodiesterases and is degraded by pancreatic ribonuclease to adenosine and the compound IIIb. The compound VII is degraded by snake venom phosphodiesterase to adenosine and the compound VI.
Publisher
Institute of Organic Chemistry & Biochemistry
Cited by
10 articles.
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