Aliphatic analogues of nucleotides: synthesis and affinity towards nucleases.
DL-1-(2,3-Dihydroxypropyl)thymine was prepared by Hilbert-Johnson reaction of 2,4-dinethoxy-5-methylpyrimidine with allyl bromide followed by the osmium tetroxide catalyzed hydroxylation of the l-allyl-4-methoxy-5-methylpyrimidin-2-one obtained as an intermediate. The D-glycero enantiomer, R-1-(2,3-dihydroxypropyl)thymine and the corresponding 1-substituted uracil derivative were prepared from 3-O-p-toluenesulfonyl-1, 2-O-isopropylidene-D-glycerine and sodium salt of 4-methoxy-5-methylpyrimidin-2-one or 4-methoxypyrimidin-2-one followed by treatment with hydrogen chloride in ethanol. The phosphorylation of the above 2,3-dihydroxypropyl derivatives with phosphoryl chloride in triethyl phosphate afforded the corresponding 3-phosphates which were transformed into the 2',3'-cyclic phosphates by the condensation with N,N'-dicyclohexylcarbodiimide. The latter compounds of the D-glycero configuration are split by some microbial RNases to the 3-phosphates.
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D000818:Animals; D002942:Circular Dichroism; D066298:In Vitro Techniques; D011742:Pyrimidine Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D012260:Ribonucleases / Q000378:metabolism; D013379:Substrate Specificity
D011742:Pyrimidine Nucleotides; D012260:Ribonucleases