Ribosyl Geometry in the Transition State of Streptococcus pneumoniae Methylthioadenosine Nucleosidase from the 3′- 2 H Kinetic Isotope Effect
Synthesis of [3'-(2)H)-labeled 5'-methylthioadenosine (MTA) derivatives permitted measurement of the [3'-(2)H) KIE of the reaction catalyzed by Streptococcus pneumoniae methylthioadenosine nucleosidase (spMTAN). The key [3'-(2)H) KIE revealed the partial 3'-OH polarization and H3'-endo -> exo ribosyl configuration at the spMTAN transition state. A new understanding of the transition state stabilization of spMTAN-catalyzed hydrolysis is uncovered in structural features at the spMTAN transition state.
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