Collect. Czech. Chem. Commun. 1984, 49, 2689-2697

Reaction of 2,2'-anhydro-1-(β-D-arabinofuranosyl)-6-azauracil, 4-chloropyrimidine and 6-chloropurine nucleosides with amino acids

Hubert Hřebabecký and Jiří Beránek

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Reaction of cycloazauridine I with glycine and L-Lysine in water at pH 10 afforded the glycine derivative II and the Nε-lysine derivative III, respectively. An identical sample of III was prepared by reaction of Nα-formyl-L-lysine with I followed by deformylation of the formed IV. L-Arginine reacts with I in water to give the Nα-derivative V. Under analogous conditions, 6-chloro-9-β-D-ribofuranosylpurine and L-lysine afford the Nε derivative X. Reaction with Nα- and Nε-formyl-L-lysine at pH 10 leads to the Nε-ribosylpurinyl derivatives XI and XII which are deformylated with hydrochloric acid to compounds X and XIII. Benzyl glycinate reacts with 4-chloro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)- and 4-chloro-1-(2,3,5-tri-O-benzoyl-β-D-arabinofuranosyl)pyrimidin-2(1H)-one in chloroform to give benzyl N-(1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrimidin-2(1H)-on-4-yl)glycinate (VI) and N-(1-(2,3,5-tri-O-benzoyl-β-D-arabinofuranosyl)pyrimidin-2(1H)-on-4-yl)glycinate (VIII). Their methanolysis with sodium methoxide afforded the free methyl glycinates VII and IX. The reaction of poly(L-lysine) with I and 6-chloro-9-β-D-ribofuranosylpurine was investigated.