Towards the synthesis of photobactin: methodology and metal binding aspects
thesisposted on 2021-05-22, 14:55 authored by Michelle Shuoprasad
Siderophores are metal-typically iron-chelating compounds that have received countless attention in research, as they can play a role in medicine intended for drug delivery and iron overload treatment. The synthesis of Photobactin has been of interest as it has been previously isolated (<10 mg) from Photorhabdus luminescence and has not once been synthesized. This thesis examined the preparation of Photobactin using a multi-step approach: synthesizing two building blocks individually and coupling them together with an amide coupling reagent. Both building blocks were synthesized successfully. However, the deprotection of the ester group on one of the building blocks has been uncooperative, and therefore the total synthesis of Photobactin was not achieved. Moreover, DFT computation calculations were performed to study Photobactin binding properties with Fe3+. According to the results, iron (Fe3+) is likely to form a hexadentate (6-coordinate ligand) or a tetradentate (4-coordinate ligand) complex with Photobactin. Each of the compounds leading to Photobactin was characterized using 1H and 13C-NMR. Some compounds were characterized using elemental analysis and performing 2D-NMR (COSY, HMBC, and HSQC) to make final assignments.