83. Nucleotide Coupling in Reverse Micelles

Article abstract of DOI:10.1002/hlca.19930760321

Nucleotide coupling was investigated in reverse micelles formed by (cetyl)trimethylammonium bromide (CTAB), in hexane/pentan-1-ol.In particular, the coupling of 2'-deoxy-5'-O-methylcytidine 3'-O-phosphate, prepared by phosphoramidite chemistry, with 5'-amino-5'-deoxythymidine was studied in the presence of a H2O-soluble carbodiimide at w0 = 11 and 22 (w0 = /).The effect of w0 on the reaction rate was investigated.A solid-phase strategy was developed for the synthesis of 2'-deoxy-5'-O-methyl-cytidyl-(3'-5')-5'-amino-5'-deoxythymidine.The nucleotide coupling yielding the expected product occurred readily in reverse micelles, and this is discussed in connection with the micelle self-replication program.