Abstract
A method for the selective reduction of dihydrouridine in transfer RNA from yeast has been developed. The chemistry of the reaction, which uses sodium borohydride as a reducing agent, was studied with dihydrouracil, dihydrouridine and dihydrouridine-2′(3′)-phosphate as starting materials. 3-Ureidopropane-1-ol, N-ribosyl-3-ureidopropane-1-ol and N-(2′(3′)-phosphorylribosyl)-3-ureidopropane-1-ol, respectively, were proved to be the major reduction products by spectral and chemical evidence. 3-Ureidopropane-1-ol was also synthesized by an independent route. In nucleotide mixtures and in yeast transfer RNA, dihydrouridine was reduced with sodium borohydride with high selectivity. The major nucleotides, pseudouridine and glucosyl-2-thiouridine, were found to be inert towards the reducing agent. N 4 -Acetyl-cytidine was reduced to N 1 -ribosyl- N 4 acetyl-3,4,5,6-tetrahydrocytidine and 4-thiouridine to N-ribosyl-2-oxohexahydropyrimidine under the conditions used for the reduction of RNA.
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