Synthesis of 4- and 5-amino-1-(2-deoxy-D-erythro-pentofuranosyl)imidazole nucleosides by chemical and biotransformation methods

Article abstract of DOI:10.1016/0008-6215(92)84154-K

(2-Deoxy-D-erythro-pentofuranosyl)imidazole nucleosides have been synthesized by glycosylation of the sodium salt of ethyl 5-aminoimidazole-4-carboxylate with 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride.Glycosylation of ethyl 5-aminoimidazole-4-carboxylate with 2-deoxy-β-D-erythro-pentofuranose was also achieved enzymically using E. colli, immobilised by ionotropic gelation in an alginate gel, with 2'-deoxyuridine as glycosyl donor. 5-Amino-1-(2-deoxy-β-D-erythro-pentofruanosyl)imidazole-4-carboxylic acid 5'-phosphate and 4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)imidazole-5-carboxylic acid 5'-phosphate were synthesised by phosphorylation of the respective nucleosides and examined as inhibitors of phosphoribosylaminoimidazole carboxylase (EC 4.1.1.21) and phosphoribosylaminoimidazolesuccinocarboxamide synthetase (EC 6.3.2.6), which are involved in the de novo biosynthesis of purine nucleotides.