Date of Award

8-2024

Document Type

Campus Access Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry/Biological Chemistry

First Advisor

Daniel P. Dowling

Second Advisor

Jason Evans

Third Advisor

Jennifer Bridwell-Rabb, Niya Sa

Abstract

Sulfur is essential for life, playing a critical role in metabolic functions and cellular signaling pathways. While bacteria typically obtain sulfur from inorganic sulfate, they must resort to alternative sources when sulfate is limited. Pseudomonads have evolved a sophisticated system to address this challenge, employing two-component flavin-dependent monooxygenases (TC-FMOs) to assimilate sulfur from alkanesulfonates and dialkylsulfones, such as dimethylsulfone (DMSO2). This process is triggered by a stress response during sulfur starvation conditions. To convert DMSO2 into bioavailable sulfite, Pseudomonads perform a series of chemical transformations regulated by the msu and sfn operons. This dissertation investigates the mechanisms underlying these transformations in Pseudomonas fluorescens, focusing on the TC-FMOs responsible for DMSO2 catabolism. The insights gained from this research have potential applications in bioremediation and may contribute to our understanding of human health in relation to other Pseudomonas species. The msu and sfn operons encode the two-component flavin-dependent monooxygenases (TC-FMOs) SfnG, MsuC, and MsuD, along with the FMN reductase MsuE, which collectively catalyzes the catabolism of dimethylsulfone (DMSO2) to sulfite. This dissertation provides an in depth structural and biophysical investigation into the function of SfnG and MsuC, which convert DMSO2 to methanesulfinate (MSI–) and MSI– to methanesulfonate (MS–), respectively. Multiple high-resolution crystal structures of SfnG revealed critical protein regions that become ordered upon binding of the ligands FMN and DMSO2. The placement of ligands identified a putative oxygen binding site, suggesting SfnG may employ an N5-(hydro)peroxyflavin for oxidative cleavage of the C–S bond of DMSO2. Functional biochemical experiments support the use of an N5-(hydro)peroxyflavin intermediate, and biophysical studies reveal the complexities of ligand binding to SfnG. The second enzyme in the pathway, MsuC, catalyzes the oxidation of MSI– to form MS– through S–O bond formation. Structural analysis confirms that MsuC belongs to the two-component flavin-dependent monooxygenase (TC-FMO) family and likely employs C4a flavin chemistry for catalysis. A high resolution unliganded structure, combined with computational studies, revealed a putative MSI– binding pocket with features that allow for binding of this negatively charged molecule. Further structural analysis, including alignments with homologous enzymes, uncovered conserved C-terminal interactions that stabilize the active site and are connected to substrate binding. These structural inferences provide a foundation for future functional studies, which will enhance our understanding of MsuC’s catalytic mechanism and substrate binding dynamics. Additionally, biophysical characterization has yielded new insights into the role of FMN binding in enzyme stability and function. The high-resolution structures of SfnG with bound FMN and DMSO2, as well as MsuC, have provided valuable insights into these enzymes. Detailed characterization of their structures and active sites enables targeted mutational analyses to elucidate substrate specificity and promiscuity. Notably, these systems are prevalent in various Pseudomonas strains, including opportunistic, multi-drug resistant pathogens like Pseudomonas aeruginosa. Given that SfnG and MsuC catalyze C–S bond cleavage and S–O bond formation, respectively, future studies could explore modulating their activities to target other compounds, such as those containing C–Si bonds or persistent environmental contaminants like polyfluoroalkyl substances (PFAS). This research not only advances our understanding of bacterial sulfur metabolism but also opens avenues for potential biotechnological and environmental applications.

Comments

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Available for download on Wednesday, September 30, 2026

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