Heparan sulfate is a complex cell-surface proteoglycan that serves many important roles in biology, such as growth and development, immune response and pathogenesis. Heparan sulfate is structurally heterogeneous due to the variable post- glycosylation modifications, particularly the generation of diverse sets of sulfate esters (sulfoforms) for any given disaccharide unit. In order to establish useful relationships between heparan sulfate structure and biological activity, a set of well-defined sulfoforms is necessary to support binding affinity screening. In this thesis, we describe the generation of diverse sulfoforms from heparan disaccharides using a fluorous tag to facilitate purification of highly charged intermediates, and their subsequent immobilizaion on substrates for affinity binding studies.
A library of heparan disaccharide sulfoforms was prepared from a single intermediate using an orthogonal protecting group system, to enable the controlled unmasking of hydroxyls or amines for subsequent sulfonation. A practical challenge of this approach is the need to carry highly polar intermediates through multiple synthetic steps. This was addressed by installing a perfluoroalkyl (fluorous) tag on the reducing end of the orthogonally protected disaccharide. The fluorous tag facilitated the separation of polar intermediates from non-fluorous byproducts via a two-stage solid-phase extraction. In this manner, a library of 1,4-linked disaccharides comprised of glucuronic acid (GlcA) and glucosamine (GlcN) could be prepared with a variable set of sulfonated substituents. The fluorous tag was retained on the final product to enable their non- covalent adhesion onto perfluoroalkyl-functionalized glass slides in microarray format, for biological screening against L-selectin, FGF2, and urokinase.
Lithium ion batteries have quickly become an important energy source and storage medium for electronics in recent years. Increasing the useful lifetime of batteries is a key challenge in their wide use. A number of perfluoroalkyl-functionalized small molecules were prepared as performance-enhancing additives for lithium ion batteries. Perfluorooctyl ethylene carbonate was identified as a candidate that had positive effects on both cell cycling and cell impedance.
","abstract_html":"<p>Heparan sulfate is a complex cell-surface proteoglycan that serves many important roles in biology, such as growth and development, immune response and pathogenesis. Heparan sulfate is structurally heterogeneous due to the variable post- glycosylation modifications, particularly the generation of diverse sets of sulfate esters (sulfoforms) for any given disaccharide unit. In order to establish useful relationships between heparan sulfate structure and biological activity, a set of well-defined sulfoforms is necessary to support binding affinity screening. In this thesis, we describe the generation of diverse sulfoforms from heparan disaccharides using a fluorous tag to facilitate purification of highly charged intermediates, and their subsequent immobilizaion on substrates for affinity binding studies.</p> <p>A library of heparan disaccharide sulfoforms was prepared from a single intermediate using an orthogonal protecting group system, to enable the controlled unmasking of hydroxyls or amines for subsequent sulfonation. A practical challenge of this approach is the need to carry highly polar intermediates through multiple synthetic steps. This was addressed by installing a perfluoroalkyl (fluorous) tag on the reducing end of the orthogonally protected disaccharide. The fluorous tag facilitated the separation of polar intermediates from non-fluorous byproducts via a two-stage solid-phase extraction. In this manner, a library of 1,4-linked disaccharides comprised of glucuronic acid (GlcA) and glucosamine (GlcN) could be prepared with a variable set of sulfonated substituents. The fluorous tag was retained on the final product to enable their non- covalent adhesion onto perfluoroalkyl-functionalized glass slides in microarray format, for biological screening against L-selectin, FGF2, and urokinase.</p> <p>Lithium ion batteries have quickly become an important energy source and storage medium for electronics in recent years. Increasing the useful lifetime of batteries is a key challenge in their wide use. A number of perfluoroalkyl-functionalized small molecules were prepared as performance-enhancing additives for lithium ion batteries. Perfluorooctyl ethylene carbonate was identified as a candidate that had positive effects on both cell cycling and cell impedance.</p>","abstract_has_math":false,"creators":["Casselman, Matthew Daniel"],"institution":null,"degree_name":"Doctor of Philosophy (PhD)","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Alexander Wei","David H. Thompson","Yu Xia","Mingji Dai"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2013,"date_issued":"2013-10-01T07:00:00Z","date_published":"2013-10-01T07:00:00Z","updated_at":"2026-07-24T03:53:02Z","subjects":["pure sciences","flourous-phase synthesis","heparan sulfate disaccharides","lithium-ion batteries","Organic Chemistry"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://docs.lib.purdue.edu/open_access_dissertations/173","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Alexander Wei","David H. Thompson","Yu Xia","Mingji Dai"]},{"key":"dc:creator","label":"Author","values":["Casselman, Matthew Daniel"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Doctor of Philosophy (PhD)"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["pure sciences","flourous-phase synthesis","heparan sulfate disaccharides","lithium-ion batteries","Organic Chemistry"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://docs.lib.purdue.edu/open_access_dissertations/173"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Heparan sulfate is a complex cell-surface proteoglycan that serves many important roles in biology, such as growth and development, immune response and pathogenesis. Heparan sulfate is structurally heterogeneous due to the variable post- glycosylation modifications, particularly the generation of diverse sets of sulfate esters (sulfoforms) for any given disaccharide unit. In order to establish useful relationships between heparan sulfate structure and biological activity, a set of well-defined sulfoforms is necessary to support binding affinity screening. In this thesis, we describe the generation of diverse sulfoforms from heparan disaccharides using a fluorous tag to facilitate purification of highly charged intermediates, and their subsequent immobilizaion on substrates for affinity binding studies.
A library of heparan disaccharide sulfoforms was prepared from a single intermediate using an orthogonal protecting group system, to enable the controlled unmasking of hydroxyls or amines for subsequent sulfonation. A practical challenge of this approach is the need to carry highly polar intermediates through multiple synthetic steps. This was addressed by installing a perfluoroalkyl (fluorous) tag on the reducing end of the orthogonally protected disaccharide. The fluorous tag facilitated the separation of polar intermediates from non-fluorous byproducts via a two-stage solid-phase extraction. In this manner, a library of 1,4-linked disaccharides comprised of glucuronic acid (GlcA) and glucosamine (GlcN) could be prepared with a variable set of sulfonated substituents. The fluorous tag was retained on the final product to enable their non- covalent adhesion onto perfluoroalkyl-functionalized glass slides in microarray format, for biological screening against L-selectin, FGF2, and urokinase.
Lithium ion batteries have quickly become an important energy source and storage medium for electronics in recent years. Increasing the useful lifetime of batteries is a key challenge in their wide use. A number of perfluoroalkyl-functionalized small molecules were prepared as performance-enhancing additives for lithium ion batteries. Perfluorooctyl ethylene carbonate was identified as a candidate that had positive effects on both cell cycling and cell impedance.
"]},{"key":"dc:title","label":"Title","values":["Fluorous- Phase Synthesis of Heparan Sulfate Disaccharides & Low-Molecular Weight Additives for Enhancing the Performance of Lithium-Ion Batteries."]}]}],"canonical_facts":{"dc:contributor":["Alexander Wei","David H. Thompson","Yu Xia","Mingji Dai"],"dc:creator":["Casselman, Matthew Daniel"],"dc:description.abstract":["Heparan sulfate is a complex cell-surface proteoglycan that serves many important roles in biology, such as growth and development, immune response and pathogenesis. Heparan sulfate is structurally heterogeneous due to the variable post- glycosylation modifications, particularly the generation of diverse sets of sulfate esters (sulfoforms) for any given disaccharide unit. In order to establish useful relationships between heparan sulfate structure and biological activity, a set of well-defined sulfoforms is necessary to support binding affinity screening. In this thesis, we describe the generation of diverse sulfoforms from heparan disaccharides using a fluorous tag to facilitate purification of highly charged intermediates, and their subsequent immobilizaion on substrates for affinity binding studies.
A library of heparan disaccharide sulfoforms was prepared from a single intermediate using an orthogonal protecting group system, to enable the controlled unmasking of hydroxyls or amines for subsequent sulfonation. A practical challenge of this approach is the need to carry highly polar intermediates through multiple synthetic steps. This was addressed by installing a perfluoroalkyl (fluorous) tag on the reducing end of the orthogonally protected disaccharide. The fluorous tag facilitated the separation of polar intermediates from non-fluorous byproducts via a two-stage solid-phase extraction. In this manner, a library of 1,4-linked disaccharides comprised of glucuronic acid (GlcA) and glucosamine (GlcN) could be prepared with a variable set of sulfonated substituents. The fluorous tag was retained on the final product to enable their non- covalent adhesion onto perfluoroalkyl-functionalized glass slides in microarray format, for biological screening against L-selectin, FGF2, and urokinase.
Lithium ion batteries have quickly become an important energy source and storage medium for electronics in recent years. Increasing the useful lifetime of batteries is a key challenge in their wide use. A number of perfluoroalkyl-functionalized small molecules were prepared as performance-enhancing additives for lithium ion batteries. Perfluorooctyl ethylene carbonate was identified as a candidate that had positive effects on both cell cycling and cell impedance.
"],"dc:identifier":["https://docs.lib.purdue.edu/open_access_dissertations/173"],"dc:subject":["pure sciences","flourous-phase synthesis","heparan sulfate disaccharides","lithium-ion batteries","Organic Chemistry"],"dc:title":["Fluorous- Phase Synthesis of Heparan Sulfate Disaccharides & Low-Molecular Weight Additives for Enhancing the Performance of Lithium-Ion Batteries."],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Doctor of Philosophy (PhD)"]},"updated_at":"2026-07-24T03:53:02Z"}