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Structural and Biosynthetic Studies on Actinobacterial Spirotetronate Natural Products
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Dissertation
Structural and Biosynthetic Studies on Actinobacterial Spirotetronate Natural Products
2022
Overview
The Diels-Alder reaction is a highly valuable reaction via which a [4+2] cycloaddition occurs to form a cyclohexene ring. Several biosynthetic enzymes, termed Diels-Alderases, have previously been shown to stereoselectively catalyse this reaction in the biosynthesis of the spirotetronate class of natural products. This spiro forming Diels-Alder reaction can have one of four stereochemical outcomes, and there are examples of all four stereochemistries in known spirotetronates. This stereocontrol is important to understand if the Diels-Alderases are to be exploited as biocatalysts that mediate stereocontrolled Diels-Alder reactions. [Figure i Generic structures of the four stereoisomeric products of the spiro forming Diels-Alder reaction in spirotetronate biosynthesis. Open circles indicate si faces, and closed circles indicate re faces involved in the overlap of the diene (blue) and the dienophile (red).] Ent-abyssomicin is a novel class I spirotetronate natural product from Streptomyces incarnatus NRRL 8089. It has been shown to be enantiomeric to the spirotetronate antibiotic abyssomicin C, resulting from an enantiodivergent Diels-Alder reaction. The structure of ent-abyssomicin was elucidated by MS, NMR, CD spectroscopy, and X-ray crystallography. The function of the Diels-Alderase involved in the biosynthesis of ent-abyssomicin has been demonstrated in vitro and the molecular basis for catalysis and stereocontrol has been investigated computationally. Also reported here is the discovery of a second biosynthetic gene cluster that produces the known class II spirotetronate MM46115. The pathway to its biosynthesis has been proposed and the compound was reisolated and structurally characterised. A DH-like domain that is proposed to install the diene required for the spiro forming Diels-Alder reaction by catalysing two consecutive dehydration reactions was studied.
Publisher
ProQuest Dissertations & Theses
Subject
