Fatty acids are compounds with limited water solubility that belong to the lipid class of bio-organic compounds and can be utilized as a source of energy by the body or as precursors to oxidized compounds that have roles in inflammation and in the regulation of vascular tone. The prostaglandins are naturally occurring 20-carbon cyclopentano fatty acid derivatives produced in mammalian tissue from polyunsaturated fatty acids (PUFAs) and are generated from endoperoxide precursors of arachidonic acid and related polyunsaturated fatty acids by the enzyme cyclo-oxygenase (COX). The lipoxygenase (LOX) enzymes convert arachidonic acid into hydroperoxy derivatives of PUFAs termed leukotrienes, which play a role in asthma and allergies. The reagent trimethyl silyl diazomethane (TMSD) which is less toxic and explosive than other reagents such as diazomethane, has been developed for use in the methyl esterification of drugs such as penicillin and some fatty acids. The objectives of the research were to (1) optimize the TMSD reaction conditions, (2) determine whether the TMSD reaction could support methylation of prostaglandins and other oxidized products of arachidonic acid, such as prostaglandins PGE2 and PGF2α, (3) develop calibration curves for the fatty acids and prostaglandins with appropriate internal standards for use with GC-MS, and (4) determine whether this method could be used to characterize by GC-MS these lipids in cell culture and in other cell-free systems, such as those containing enzymes like COX.
","abstract_html":"<p>Fatty acids are compounds with limited water solubility that belong to the lipid class of bio-organic compounds and can be utilized as a source of energy by the body or as precursors to oxidized compounds that have roles in inflammation and in the regulation of vascular tone. The prostaglandins are naturally occurring 20-carbon cyclopentano fatty acid derivatives produced in mammalian tissue from polyunsaturated fatty acids (PUFAs) and are generated from endoperoxide precursors of arachidonic acid and related polyunsaturated fatty acids by the enzyme cyclo-oxygenase (COX). The lipoxygenase (LOX) enzymes convert arachidonic acid into hydroperoxy derivatives of PUFAs termed leukotrienes, which play a role in asthma and allergies. The reagent trimethyl silyl diazomethane (TMSD) which is less toxic and explosive than other reagents such as diazomethane, has been developed for use in the methyl esterification of drugs such as penicillin and some fatty acids. The objectives of the research were to (1) optimize the TMSD reaction conditions, (2) determine whether the TMSD reaction could support methylation of prostaglandins and other oxidized products of arachidonic acid, such as prostaglandins PGE2 and PGF2α, (3) develop calibration curves for the fatty acids and prostaglandins with appropriate internal standards for use with GC-MS, and (4) determine whether this method could be used to characterize by GC-MS these lipids in cell culture and in other cell-free systems, such as those containing enzymes like COX.</p>","abstract_has_math":false,"creators":["Sengupta, Aditi Munmun"],"institution":null,"degree_name":"Master of Science (MS)","degree_level":"Open Access Thesis","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Steven J. Pernecky, PhD, chair","Ruth Ann Armitage, PhD","George Liepa, PhD, FACN"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2007,"date_issued":"2007-07-20T07:00:00Z","date_published":"2007-07-20T07:00:00Z","updated_at":"2026-07-24T02:16:57Z","subjects":["Chemistry"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://commons.emich.edu/theses/522","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Steven J. Pernecky, PhD, chair","Ruth Ann Armitage, PhD","George Liepa, PhD, FACN"]},{"key":"dc:creator","label":"Author","values":["Sengupta, Aditi Munmun"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["2013-09-25T07:00:00Z"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Open Access Thesis"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science (MS)"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://commons.emich.edu/theses/522"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Fatty acids are compounds with limited water solubility that belong to the lipid class of bio-organic compounds and can be utilized as a source of energy by the body or as precursors to oxidized compounds that have roles in inflammation and in the regulation of vascular tone. The prostaglandins are naturally occurring 20-carbon cyclopentano fatty acid derivatives produced in mammalian tissue from polyunsaturated fatty acids (PUFAs) and are generated from endoperoxide precursors of arachidonic acid and related polyunsaturated fatty acids by the enzyme cyclo-oxygenase (COX). The lipoxygenase (LOX) enzymes convert arachidonic acid into hydroperoxy derivatives of PUFAs termed leukotrienes, which play a role in asthma and allergies. The reagent trimethyl silyl diazomethane (TMSD) which is less toxic and explosive than other reagents such as diazomethane, has been developed for use in the methyl esterification of drugs such as penicillin and some fatty acids. The objectives of the research were to (1) optimize the TMSD reaction conditions, (2) determine whether the TMSD reaction could support methylation of prostaglandins and other oxidized products of arachidonic acid, such as prostaglandins PGE2 and PGF2α, (3) develop calibration curves for the fatty acids and prostaglandins with appropriate internal standards for use with GC-MS, and (4) determine whether this method could be used to characterize by GC-MS these lipids in cell culture and in other cell-free systems, such as those containing enzymes like COX.
"]},{"key":"dc:title","label":"Title","values":["Methyl esterification of fatty acids and eicosanoids with a novel reagent trimethylsilyldiazomethane for analysis by gas chromatography-mass spectrometry"]}]}],"canonical_facts":{"dc:contributor":["Steven J. Pernecky, PhD, chair","Ruth Ann Armitage, PhD","George Liepa, PhD, FACN"],"dc:creator":["Sengupta, Aditi Munmun"],"dc:date.available":["2013-09-25T07:00:00Z"],"dc:description.abstract":["Fatty acids are compounds with limited water solubility that belong to the lipid class of bio-organic compounds and can be utilized as a source of energy by the body or as precursors to oxidized compounds that have roles in inflammation and in the regulation of vascular tone. The prostaglandins are naturally occurring 20-carbon cyclopentano fatty acid derivatives produced in mammalian tissue from polyunsaturated fatty acids (PUFAs) and are generated from endoperoxide precursors of arachidonic acid and related polyunsaturated fatty acids by the enzyme cyclo-oxygenase (COX). The lipoxygenase (LOX) enzymes convert arachidonic acid into hydroperoxy derivatives of PUFAs termed leukotrienes, which play a role in asthma and allergies. The reagent trimethyl silyl diazomethane (TMSD) which is less toxic and explosive than other reagents such as diazomethane, has been developed for use in the methyl esterification of drugs such as penicillin and some fatty acids. The objectives of the research were to (1) optimize the TMSD reaction conditions, (2) determine whether the TMSD reaction could support methylation of prostaglandins and other oxidized products of arachidonic acid, such as prostaglandins PGE2 and PGF2α, (3) develop calibration curves for the fatty acids and prostaglandins with appropriate internal standards for use with GC-MS, and (4) determine whether this method could be used to characterize by GC-MS these lipids in cell culture and in other cell-free systems, such as those containing enzymes like COX.
"],"dc:identifier":["https://commons.emich.edu/theses/522"],"dc:subject":["Chemistry"],"dc:title":["Methyl esterification of fatty acids and eicosanoids with a novel reagent trimethylsilyldiazomethane for analysis by gas chromatography-mass spectrometry"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Open Access Thesis"],"thesis:degree_name":["Master of Science (MS)"]},"updated_at":"2026-07-24T02:16:57Z"}