Intrinsic selectivity in some prebiotic reactions of urazole with sugars

Details Intrinsic selectivity in some prebiotic reactions of urazole with sugars Intrinsic selectivity in some prebiotic reactions of urazole with sugars

Feb 2004

adsabs.harvard.edu/cgi-bin/nph-data_query?bibcode=2004spie.5163...48k&link_type=abstract

Instruments, Methods, and Missions for Astrobiology VII. Edited by Hoover, Richard B.; Rozanov, Alexei Y. Proceedings of the

Biology

Scientific paper

Urazole (1,2,4-triazolidine-3,5-dione) (1), 4-methylurazole (12), and its carbon analog, 4,4-dimethylpyrazolidine-3,5-dione (18), react with 2-deoxy-D-ribose (2-deoxy-D-erythro-pentose; 6) in an aqueous solution at room temperature in a regioselective manner (a single substitution on a hydrazidic nitrogen, no reaction on the imide nitrogen) to give a mixture of four nucleosides. These are α and β pyranosides (p) and α and β furanosides (f). The α p forms in a stereoselective manner. A crystalline precipitate is formed in each of the above reactions, which is an exclusive enantiospecific product, 1R, 2R α p. 1 with 2-deoxy-L-ribose (10) gives a precipitate with the exclusive 1S, 2S α p stereochemistry. With 2-deoxy-D-glucose (2-deoxy-D-arabino-hexose; 7) the reaction with 1 is stereospecific, since only one isomer, β p, forms in the solution. Causes of enhanced reactivity of 1 with sugars were also studied. It was found that cyclic hydrazide analogs of 1, such as 12 and 18, are reactive, but open-chain analogs, 1,2,-diacetylhydrazine (21) and 1,2-dicarbethoxyhydrazine (22), are not. Although this reactivity assessment was done qualitatively and under restrictive reaction conditions, it still may be valuable for understanding α -effect of hydrazide nucleophiles. The prebiotic significance of our results is discussed.

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