Synthesis and Antimicrobial Activity of 2′-Deoxypuromycin

Synthesis of Conformationally Locked Versions of Puromycin Analogues

“…Although the proposed target compounds lack the 2′-OH, the bicyclo[3.1.0]hexane ring system is able to precisely confine the conformation of the pseudosugar regardless of the presence of the 2′-OH. In 1990 Koizumi et al synthesized 2′-deoxypuromycin and suggested that the weaker antimicrobial properties of the compound were due to a conformational dominance of the South conformation in contrast to puromycin’s North conformation that was revealed by proton NMR 7. Hence, the target compounds ( 4 & 5 and 8 & 9 ) are proposed to reliably test whether the puckering of the sugar ring changes the orientation of the aminoacyl moiety of puromycin and how it influences the recognition by peptidyl transferase at the active site.…”