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The Diels-Alder reaction is an important synthetic transformation involving the [4 + 2]cycloaddition of a diene and dienophile to construct cyclohexene rings with up to four new stereocentres. This reaction has been extensively applied in the total synthesis of complex natural product scaffolds but achieving high selectivity under mild conditions is often challenging. This thesis describes investigations on Diels-Alderase enzymes from tetronate biosynthetic pathways to probe enzyme selectivity and explore their potential use as biocatalysts.
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