The permanganate oxidation of thymidine

Abstract

Thymidine was oxidised with potassium permanganate at pH 8.5 at 37° and the products separated by paper chromatography. The following were identified: 5,6-dihydroxy-5,6-dihydrothymidine (‘thymidine glycol’), N-(2-deoxy-D-ribofuranosyl)-N′-pyruvoylurea, N-formylurea, and urea. A component, probably 2-deoxy-D-ribofuranosylurea was detected but it amounted to less than 4% of the reaction products. In addition were present three acidic products probably produced by the oxidation of the primary alcohol group at position 5′. Almost no 2-deoxy-D-ribose was present so it apparently must also have been oxidised to acidic products. 5,6-Dihydroxy-5,6-dihydrothymidine was obtained also by oxidation of thymidine with osmium tetroxide and barium chlorate.