{"id":{"repo_id":"nus","oai_identifier":"oai:scholarbank.nus.edu.sg:10635/121731"},"canonical_url":"https://search.dev.ndltd.org/etd/nus/oai:scholarbank.nus.edu.sg:10635/121731","repository":{"repo_id":"nus","name":"National University of Singapore","base_url":"https://scholarbank.nus.edu.sg/oai/request"},"display":{"title":"CHEMICAL SYNTHESIS AND BIOLOGICAL EVALUATION OF CHONDROITIN SULFATE DISACCHARIDES","abstract":"Glycosaminoglycans (GAGs) are heterogeneous polysaccharides comprising of repeating uronic acid and amino sugar disaccharide units. Recently, it was shown that the sulfate groups present in chondroitin sulfate GAGs (CS) encode important functional information for the regulation of physiological processes. However, procurement of pure, homogenous CS motifs for biological evaluation is a challenging task due to isolation difficulty and structural complexity. To probe the ?sulfation code? in CS, a synthetic strategy was devised to obtain all 16 theoretically possible sulfation patterns in the CS repeat unit. The strategy incorporates orthogonal protecting groups in glucuronic acid and N-acetyl galactosamine precursor units obtained through a divergent approach, prior to modular glycosylation and selective final transformations. Biological evaluation indicated that CS sulfation patterns had differing effects for different breast cancer cell types, and the greatest inhibitory effect was observed for the most aggressive, triple negative breast cancer cell line MDA-MB-231.","abstract_html":"Glycosaminoglycans (GAGs) are heterogeneous polysaccharides comprising of repeating uronic acid and amino sugar disaccharide units. Recently, it was shown that the sulfate groups present in chondroitin sulfate GAGs (CS) encode important functional information for the regulation of physiological processes. However, procurement of pure, homogenous CS motifs for biological evaluation is a challenging task due to isolation difficulty and structural complexity. To probe the ?sulfation code? in CS, a synthetic strategy was devised to obtain all 16 theoretically possible sulfation patterns in the CS repeat unit. The strategy incorporates orthogonal protecting groups in glucuronic acid and N-acetyl galactosamine precursor units obtained through a divergent approach, prior to modular glycosylation and selective final transformations. Biological evaluation indicated that CS sulfation patterns had differing effects for different breast cancer cell types, and the greatest inhibitory effect was observed for the most aggressive, triple negative breast cancer cell line MDA-MB-231.","abstract_has_math":false,"creators":["POH ZHONG WEI"],"institution":null,"degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2015,"date_issued":"2015-07-31","date_published":"2015-07-31","updated_at":"2026-07-24T03:32:18Z","subjects":["Chemical synthesis, Carbohydrate chemistry, Library Synthesis, Chondroitin sulfate, Sulfation code, Breast cancer"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":null,"outbound_label":null,"outbound_source":null},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["POH ZHONG WEI"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.issued","label":"Date","values":["2015-07-31"]},{"key":"dc:relation.isreferencedby","label":"Dc Relation Isreferencedby","values":["https://scholarbank.nus.edu.sg/handle/10635/121731"]},{"key":"dc:type","label":"Dc Type","values":["Thesis"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemical synthesis, Carbohydrate chemistry, Library Synthesis, Chondroitin sulfate, Sulfation code, Breast cancer"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://scholarbank.nus.edu.sg/bitstreams/55c75e30-15b4-4ab9-94ab-56972d3be621/download"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Glycosaminoglycans (GAGs) are heterogeneous polysaccharides comprising of repeating uronic acid and amino sugar disaccharide units. Recently, it was shown that the sulfate groups present in chondroitin sulfate GAGs (CS) encode important functional information for the regulation of physiological processes. However, procurement of pure, homogenous CS motifs for biological evaluation is a challenging task due to isolation difficulty and structural complexity. To probe the ?sulfation code? in CS, a synthetic strategy was devised to obtain all 16 theoretically possible sulfation patterns in the CS repeat unit. The strategy incorporates orthogonal protecting groups in glucuronic acid and N-acetyl galactosamine precursor units obtained through a divergent approach, prior to modular glycosylation and selective final transformations. Biological evaluation indicated that CS sulfation patterns had differing effects for different breast cancer cell types, and the greatest inhibitory effect was observed for the most aggressive, triple negative breast cancer cell line MDA-MB-231."]},{"key":"dc:format.checksum.md5","label":"Dc Format Checksum Md5","values":["04a85142947eaac04f0bef41772ff4e3","0a3cdddf68d816089ee488a94ca5103e"]},{"key":"dc:title","label":"Title","values":["CHEMICAL SYNTHESIS AND BIOLOGICAL EVALUATION OF CHONDROITIN SULFATE DISACCHARIDES"]}]}],"canonical_facts":{"dc:creator":["POH ZHONG WEI"],"dc:date.issued":["2015-07-31"],"dc:description.abstract":["Glycosaminoglycans (GAGs) are heterogeneous polysaccharides comprising of repeating uronic acid and amino sugar disaccharide units. Recently, it was shown that the sulfate groups present in chondroitin sulfate GAGs (CS) encode important functional information for the regulation of physiological processes. However, procurement of pure, homogenous CS motifs for biological evaluation is a challenging task due to isolation difficulty and structural complexity. To probe the ?sulfation code? in CS, a synthetic strategy was devised to obtain all 16 theoretically possible sulfation patterns in the CS repeat unit. The strategy incorporates orthogonal protecting groups in glucuronic acid and N-acetyl galactosamine precursor units obtained through a divergent approach, prior to modular glycosylation and selective final transformations. Biological evaluation indicated that CS sulfation patterns had differing effects for different breast cancer cell types, and the greatest inhibitory effect was observed for the most aggressive, triple negative breast cancer cell line MDA-MB-231."],"dc:format.checksum.md5":["04a85142947eaac04f0bef41772ff4e3","0a3cdddf68d816089ee488a94ca5103e"],"dc:identifier.uri":["https://scholarbank.nus.edu.sg/bitstreams/55c75e30-15b4-4ab9-94ab-56972d3be621/download"],"dc:relation.isreferencedby":["https://scholarbank.nus.edu.sg/handle/10635/121731"],"dc:subject":["Chemical synthesis, Carbohydrate chemistry, Library Synthesis, Chondroitin sulfate, Sulfation code, Breast cancer"],"dc:title":["CHEMICAL SYNTHESIS AND BIOLOGICAL EVALUATION OF CHONDROITIN SULFATE DISACCHARIDES"],"dc:type":["Thesis"]},"updated_at":"2026-07-24T03:32:18Z"}