Lignan Project - Revision history

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Electron Density Analysis of Lignin Monomer-Like Molecules

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Electron Density Analysis of Lignin Monomer-Like Molecules

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 ''<small>The following document was completed by Taylor Coffman in Spring of 2021 in partial fulfillment of her requirements for a Bachelor's Degree of Science in Biochemistry, Monmouth College, Monmouth, Il 61462. The research was done under the supervision of Bradley E. Sturgeon.</small>''
 ==Abstract==
 Lignin monomers can couple to form a large organic polymer or dimerize to form lignan. Lignan is a biologically active compound with various uses in the medical field, but lignan itself is extremely expensive for use in an undergraduate lab, with standards ranging in the upper three figures. An easily obtained product claiming to contain a certain lignan, hydroxymatairesinol, is available for purchase on the retailer Amazon.com for a low cost compared to commercially available standards. Purification, concentration, and eventual characterization of this material may lead to the availability of a lignan for use in undergraduate research labs. Use of HPLC and computational techniques (Gaussian and WINSIM) may lead to further understanding of the oxidative coupling of these monomers and could eventually lead to the commercial production of different lignans.
 ==Abstract==

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 ==Introduction==
-Lignin is an abundant, complex organic polymer that acts as one of the principle components of plants. Lignin plays a role in the structure of plant cell walls, works to move water through the plant to critical areas and helps to prevent water evaporation.<ref>[[:Media:Dimmel Overview.pdf|Dimmel, D. (2010). Overview. ''Lignin and Lignans Advances in Chemistry.'' Taylor & Francis Group.]]</ref> Lignins account for a large percentage of overall plant mass, at around 20-25%.<ref>[[:Media:Lignan and Lignan Biosynthesis.pdf|Lewis, N. G., Davin, L. B., & Sarkanen, S. (1998) Lignan and Lignan Biosynthesis: Distinctions and Reconciliations. ''American Chemical Society Symposium Series'', 1-27.]]</ref> We know that lignin does not act alone in it’s structural duties, commonly forming complexes with polymeric carbohydrates.<ref>[[:Media:Dimmel Overview.pdf|Dimmel, D. (2010). Overview. ''Lignin and Lignans Advances in Chemistry.'' Taylor & Francis Group.]]</ref> Difficulty in isolating lignin from these lignin-carbohydrate complexes means that synthetic lignins are commonly used for research purposes. The basic monomers that make up the lignin polymer are p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol. These three monomers are phenylpropane units that differ in their substitutions at the 3 and 5 positions.<ref>[[:Media:Dimmel Overview.pdf|Dimmel, D. (2010). Overview. ''Lignin and Lignans Advances in Chemistry.'' Taylor & Francis Group.]]</ref> In the case of lignin nomenclature, the side chain attachment to the aromatic ring is considered position C-1 and the phenol group considered to be position C-4. These monomeric alcohols undergo oxidative coupling with each other and with a growing polymer end unit.<ref>[[:Media:Dimmel Overview.pdf|Dimmel, D. (2010). Overview. ''Lignin and Lignans Advances in Chemistry.'' Taylor & Francis Group.]]</ref> This oxidation process results in radicals delocalized at positions C-1, C-3, C-5, C-β, and O-4.<ref>[[:Media:Dimmel Overview.pdf|Dimmel, D. (2010). Overview. ''Lignin and Lignans Advances in Chemistry.'' Taylor & Francis Group.]]</ref> The most frequently formed bonds are β-O-4 bonds.<ref>[[:Media:Dimmel Overview.pdf|Dimmel, D. (2010). Overview. ''Lignin and Lignans Advances in Chemistry.'' Taylor & Francis Group.]]</ref>
+Lignin is an abundant, complex organic polymer that acts as one of the principle components of plants. Lignin plays a role in the structure of plant cell walls, works to move water through the plant to critical areas and helps to prevent water evaporation.
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 ==Abstract==
-Lignin monomers can couple to form large organic polymers (lignin) or dimerize to form a lignan. Lignans are biologically active compounds of interest in medical research, although lignans are not readily available and are expensive. An easily obtained product claiming to contain the lignan, hydroxymatairesinol, is available for purchase from Amazon.com. This project will outline the purification, concentration, and eventual characterization of this material will allow for other medical-related lignan research projects. HPLC analysis and computational techniques (Gaussian and WINSIM) will be presented to further understanding of the oxidative coupling of these monomers with the hope of providing insights that could lead to the commercial production of various lignans.
+Lignin monomers can couple to form large organic polymers (lignin) or dimerize to form a lignan. Lignans are biologically active compounds of interest in medical research, although lignans are not readily available and are expensive. An easily obtained product claiming to contain the lignan, hydroxymatairesinol, is available for purchase from Amazon.com. This project will outline the purification, concentration, and eventual characterization of this material to allow for other medical-related lignan research projects. HPLC analysis and computational techniques (Gaussian and WINSIM) will be presented to further understanding of the oxidative coupling of these monomers with the hope of providing insights that could lead to the commercial production of various lignans.
 ==Introduction==

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 ==Abstract==
-Lignin monomers can couple to form a large organic polymer (lignin) or dimerize to form a lignan. Lignans are biologically active compounds of interest in medical research, although lignans are not readily available and are expensive. An easily obtained product claiming to contain the lignan, hydroxymatairesinol, is available for purchase from Amazon.com. This project will outline the purification, concentration, and eventual characterization of this material will allow for other medical-related lignan research projects. HPLC analysis and computational techniques (Gaussian and WINSIM) will be presented to further understanding of the oxidative coupling of these monomers with the hope of providing insights that could lead to the commercial production of various lignans.
+Lignin monomers can couple to form large organic polymers (lignin) or dimerize to form a lignan. Lignans are biologically active compounds of interest in medical research, although lignans are not readily available and are expensive. An easily obtained product claiming to contain the lignan, hydroxymatairesinol, is available for purchase from Amazon.com. This project will outline the purification, concentration, and eventual characterization of this material will allow for other medical-related lignan research projects. HPLC analysis and computational techniques (Gaussian and WINSIM) will be presented to further understanding of the oxidative coupling of these monomers with the hope of providing insights that could lead to the commercial production of various lignans.
 ==Introduction==

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 ==Abstract==
-Lignin monomers can couple to form a large organic polymer (lignin) or dimerize to form a lignan. Lignans are biologically active compounds of interest in medical research, although lignans are not readily available and are expensive. An easily obtained product claiming to contain a the lignan, hydroxymatairesinol, is available for purchase from Amazon.com. Purification, concentration, and eventual characterization of this material may lead to the availability of a lignan for use in undergraduate research labs. Use of HPLC and computational techniques (Gaussian and WINSIM) may lead to further understanding of the oxidative coupling of these monomers and could eventually lead to the commercial production of different lignans.
+Lignin monomers can couple to form a large organic polymer (lignin) or dimerize to form a lignan. Lignans are biologically active compounds of interest in medical research, although lignans are not readily available and are expensive. An easily obtained product claiming to contain the lignan, hydroxymatairesinol, is available for purchase from Amazon.com. This project will outline the purification, concentration, and eventual characterization of this material will allow for other medical-related lignan research projects. HPLC analysis and computational techniques (Gaussian and WINSIM) will be presented to further understanding of the oxidative coupling of these monomers with the hope of providing insights that could lead to the commercial production of various lignans.
 ==Introduction==

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 ===Electron Density Analysis of Lignin Monomer-Like Molecules===
 Geometry Optimization and Molecular Orbital calculations were performed on Phenoxyl and 5-Vinylphenoxyl in WebMO using the B3YLP theory, accurate: 6-311+G(2d,p) basis set, and a density=current keyword. Hyperfine coupling constants were entered into WINSIM in order to predict EPR Spectra.
 ==Results and Discussion==