SYNTHESIS, MOLECULAR AND CRYSTAL-STRUCTURE OF 3'-N-ALKYLAMINO-3'-DEOXYTHYMIDINES AND SOME BIOCHEMICAL-PROPERTIES OF THEIR PHOSPHORUS ESTERS

Two approaches for tile synthesis of 3'-N-alkylated 3'-amino-3'deoxyth ymidines were developed, including both tile reaction of 3'-amino-3'de oxythymidine with aldehydes followed by tile sodium borohydride reduct ion and preparation of tile triphenylphosphinimine derivative and subs equent reaction with alkyl iodide. 5'-Triphosphates of tile synthesize d compounds were shown to be terminating substrates for human immunode ficiency virus and avian myeloblastosis virus reverse transcriptases a s well as for DNA polymerase beta from rat liver. At the same time the se compounds did not demonstrate tile properties of a terminating subs trate ill DNA synthesis catalyzed by human DNA polymerases alpha, epsi lon, and 1 from E. coli.