Reactions of Magnesium and Zinc Salts with Acetol and Carbon Dioxide as Models for Catalysis by Rubisco

Date of Award

2008

Document Type

Thesis

Degree Name

Bachelors

Department

Natural Sciences

First Advisor

Sherman, Suzanne

Keywords

Rubisco, Mimic, Carbon Dioxide

Area of Concentration

Chemistry

Abstract

The ribulose-1,5-bisphosphate carboxylase/oxygenase (RuBisCO) enzyme catalyzes the carboxylation of ribulose-1,5-bisphosphate (RuBP) during the Calvin cycle of photosynthesis. A functional model of this system may provide opportunities for the industrial synthesis of new carbon-carbon bonds while simultaneously reducing net carbon dioxide output. Previous research has shown that the magnesium-bound complex triazacyclononane-monoacetate (MgTCMA) is able to mimic the first step in the mechanism at the RuBisCO active site. Results indicated that MgTCMA helped promote a deuterium exchange reaction of acetol�s methyl and hydroxymethyl protons as confirmed by 1H-NMR spectroscopy. Subsequent research showed that the simple magnesium salt, Mg(O3SCF3)2, catalyzed the same reaction. The goal of this research was to determine if magnesium and zinc salts reacted with acetol and carbon dioxide can further model the active site of RuBisCO and result in formation of new carbon-carbon bonds. Decreases in proton resonances over time indicate that acetol is rapidly deuterated in the presence of Mg (O3SCF3)2 and Zn(O3SCF3)2 and base with multiple turnovers. However, upon the addition of carbon dioxide, no changes in 13C-NMR resonances were observed for acetol or carbon dioxide. The increases in acidity due to carbon dioxide decrease the reactivity of these systems. However, even when the basicity was increased, no reaction with carbon dioxide was observed.

Rights

This bibliographic record is available under the Creative Commons CC0 public domain dedication. The New College of Florida, as creator of this bibliographic record, has waived all rights to it worldwide under copyright law, including all related and neighboring rights, to the extent allowed by law.

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