Synthesis of carbocyclic nucleotides as potential substrates for thymidylate kinase.
Enantiomerically pure carbocyclic 2'-deoxy-3'-azidothymidine monophosphate (AZTMP) and carba-2'deoxy-3'-thiocyanatothymidine monophosphate were synthesized to study their behavior toward their phosphorylation by thymidylate kinase. The nucleotides were synthesized starting from the parent nucleosides by an alkaline hydrolysis of the corresponding cycloSal-phosphate triesters.
Ludek
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Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, Hamburg D-20146, Germany.
Meier
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D000970:Antineoplastic Agents / Q000138:chemical synthesis; D000998:Antiviral Agents / Q000138:chemical synthesis; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D002626:Chemistry, Pharmaceutical / Q000379:methods; D054306:Dideoxynucleotides; D015195:Drug Design; D006868:Hydrolysis; D008956:Models, Chemical; D009703:Nucleoside-Phosphate Kinase / Q000737:chemistry* / Q000378:metabolism; D009711:Nucleotides / Q000737:chemistry*; D013379:Substrate Specificity; D013942:Thymine Nucleotides / Q000737:chemistry / Q000494:pharmacology*; D015215:Zidovudine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D054306:Dideoxynucleotides; D009711:Nucleotides; D013942:Thymine Nucleotides; C057287:3'-azido-3'-deoxythymidine 5'phosphate; D015215:Zidovudine; D002244:Carbon; D009703:Nucleoside-Phosphate Kinase; C020093:dTMP kinase