Synthesis and evaluation of 2′-Deoxymugineic acid for lead remediation
Document Type
Event
Faculty Mentor
Angus Koller
Abstract
For many years, lead was used in industrial paint, pipes, wine, and other everyday items. Following the discovery of its toxicity, impact on health, children’s development, and the environment, lead contamination became a major public health concern. In Portland, Maine, lead has remained at high levels in the soil due to its common use in residential paint and industrial activities during the 1970s. Lead remediation is challenging due to lead’s chemical stability and insolubility in soil, and conventional options are often an expensive process. As an alternative, phytoremediation is a process that utilizes plants to eliminate chemicals from the soil. However, most plants only passively uptake lead, most likely mistaking it for zinc, leading to poor remediation in some locations. Grasses (graminaceae) naturally produce 2′-Deoxymugineic acid (DMA), a compound that chelates iron(III) from the soil and transports it to the leaves to aid in the production of chlorophyll. By implementing small chemical modifications to the structure of DMA, the Koller lab aims to produce a molecule capable of binding lead and transporting it through plants’ natural iron uptake pathways to actively remove lead from contaminated soils. To compare the effectiveness of a lead-binding analog of DMA, synthesizing 2′-deoxymugineic acid is crucial. Herein, we describe the synthesis of 2’-deoxymugeneic acid and assess its thermodynamic, kinetic, and structural properties for the binding of iron and lead towards the development of new remediation techniques. The structure of the synthesized 2′-deoxymugineic acid will be confirmed using nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and X-ray crystallography. Thermodynamic properties will be tested to evaluate the binding affinities of DMA for lead and iron. Kinetic experimentation will determine the rate of lead–DMA complex formation, providing insight into whether the process occurs rapidly enough to serve as a practical remediation strategy. Finally, a phytoremediation experiment using grass shoots will be conducted to quantify the extent of lead and iron uptake.
Synthesis and evaluation of 2′-Deoxymugineic acid for lead remediation
For many years, lead was used in industrial paint, pipes, wine, and other everyday items. Following the discovery of its toxicity, impact on health, children’s development, and the environment, lead contamination became a major public health concern. In Portland, Maine, lead has remained at high levels in the soil due to its common use in residential paint and industrial activities during the 1970s. Lead remediation is challenging due to lead’s chemical stability and insolubility in soil, and conventional options are often an expensive process. As an alternative, phytoremediation is a process that utilizes plants to eliminate chemicals from the soil. However, most plants only passively uptake lead, most likely mistaking it for zinc, leading to poor remediation in some locations. Grasses (graminaceae) naturally produce 2′-Deoxymugineic acid (DMA), a compound that chelates iron(III) from the soil and transports it to the leaves to aid in the production of chlorophyll. By implementing small chemical modifications to the structure of DMA, the Koller lab aims to produce a molecule capable of binding lead and transporting it through plants’ natural iron uptake pathways to actively remove lead from contaminated soils. To compare the effectiveness of a lead-binding analog of DMA, synthesizing 2′-deoxymugineic acid is crucial. Herein, we describe the synthesis of 2’-deoxymugeneic acid and assess its thermodynamic, kinetic, and structural properties for the binding of iron and lead towards the development of new remediation techniques. The structure of the synthesized 2′-deoxymugineic acid will be confirmed using nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and X-ray crystallography. Thermodynamic properties will be tested to evaluate the binding affinities of DMA for lead and iron. Kinetic experimentation will determine the rate of lead–DMA complex formation, providing insight into whether the process occurs rapidly enough to serve as a practical remediation strategy. Finally, a phytoremediation experiment using grass shoots will be conducted to quantify the extent of lead and iron uptake.
