Synthesis of polynucleotides which contain 3,N4-ethanocytidine, a nucleoside modification resulting from the action of bis(chloroethyl)-nitrosourea.
BCNU,N,N1-bis(2-chloroethyl)-N-nitrosourea is known to produce 3-hydroxyethylcytidine and 3,N4-ethanocytidine when it reacts with polycytidylic acid. The nucleoside, 3,N4-ethanocytidine, presumably results from cyclization of 3-chloroethylcytidine formed initially by transfer of chloroethyl carboniumions from BCNU to cytidine. In order to study the significance of this unusual derivative, we have synthesized 3,N4-ethanocytidine and converted it to the corresponding 5'-mono- and diphosphates. 3,N4-Ethanocytidine diphosphate has been successfully converted to a high molecular weight polymer.
D055598:Chemical Phenomena; D002621:Chemistry; D003562:Cytidine / Q000031:analogs & derivatives*; D003597:Cytosine Nucleotides; D005038:Ethylnitrosourea / Q000031:analogs & derivatives*; D009607:Nitrosourea Compounds / Q000031:analogs & derivatives*; D011119:Polynucleotides / Q000138:chemical synthesis*
D003597:Cytosine Nucleotides; D009607:Nitrosourea Compounds; D011119:Polynucleotides; D003562:Cytidine; D005038:Ethylnitrosourea