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Peter H. Seeberger. Palmacci, Emma Rose, 1976- Massachusetts Institute of Technology. Dept. of Chemistry. Massachusetts Institute of Technology. Department of Chemistry 2006-03-24T16:10:56Z 2006-03-24T16:10:56Z 2003 2003 http://hdl.handle.net/1721.1/29643 53405620 Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2003. Vita. Includes bibliographical references. Glycosaminoglycans are crucial components of the extracellular matrix and cell surface and access to define sequences is required to fully appreciate their role in biology. As is the case with most complex polysaccharides, the chemical synthesis of glycosaminoglycan structures is challenging. This thesis describes efforts towards the construction of oligosaccharides with the ultimate goal of the automated synthesis of glycosaminoglycans. The use of glycosyl phosphates of glucosamine and glucuronic acid as competent glycosylating agents is illustrated. Further expansion of the glycosyl phosphates methodology to the construction of C-aryl and C-alkyl glycosides and resulted in the synthesis of the natural product 8,1 0-di-O-methylbergenin. The automated solid-phase synthesis of two complex oligosaccharides is described. The complex-type high mannose trisaccharide and the proteoglycan linkage region tetrasaccharide were synthesized in a fully automated fashion. The efforts towards the synthesis of two glycosaminoglycans - hyaluronic acid and chondroitin sulfate - are discussed. The work focuses on the discovery of a glycosylating agent suitable for the automated solid-phase synthesis. The synthesis of glucuronic acid from glucose is described using an oxidation procedure not previously explored in oligosaccharide construction. by Emma Rose Palmacci. Ph.D. 259 p. 7788939 bytes 7788740 bytes application/pdf application/pdf eng Massachusetts Institute of Technology M.I.T. theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission. http://dspace.mit.edu/handle/1721.1/7582 Chemistry. Toward the automated synthesis of carbohydrates and glycosaminoglycans Thesis application/pdf false Publication unknown unknown <Publication xmlns="https://www.openaire.eu/cerif-profile/1.1/" id="a7736ac6-6edb-4176-a921-7ef45b4f9c12"> <Type xmlns="https://www.openaire.eu/cerif-profile/vocab/COAR_Publication_Types">http://purl.org/coar/resource_type/c_1843</Type> <Language>eng</Language> <Title>Toward the automated synthesis of carbohydrates and glycosaminoglycans</Title> <PublishedIn> <Publication> </Publication> </PublishedIn> <PublicationDate>2003</PublicationDate> <Authors> <Author> <DisplayName>Palmacci, Emma Rose, 1976-</DisplayName> <Affiliation> <OrgUnit> </OrgUnit> </Affiliation> </Author> </Authors> <Editors> </Editors> <Publishers> <Publisher> <DisplayName>Massachusetts Institute of Technology</DisplayName> <OrgUnit /> </Publisher> </Publishers> <License>http://dspace.mit.edu/handle/1721.1/7582</License> <Keyword>Chemistry.</Keyword> <Abstract>Glycosaminoglycans are crucial components of the extracellular matrix and cell surface and access to define sequences is required to fully appreciate their role in biology. As is the case with most complex polysaccharides, the chemical synthesis of glycosaminoglycan structures is challenging. This thesis describes efforts towards the construction of oligosaccharides with the ultimate goal of the automated synthesis of glycosaminoglycans. The use of glycosyl phosphates of glucosamine and glucuronic acid as competent glycosylating agents is illustrated. Further expansion of the glycosyl phosphates methodology to the construction of C-aryl and C-alkyl glycosides and resulted in the synthesis of the natural product 8,1 0-di-O-methylbergenin. The automated solid-phase synthesis of two complex oligosaccharides is described. The complex-type high mannose trisaccharide and the proteoglycan linkage region tetrasaccharide were synthesized in a fully automated fashion. The efforts towards the synthesis of two glycosaminoglycans - hyaluronic acid and chondroitin sulfate - are discussed. The work focuses on the discovery of a glycosylating agent suitable for the automated solid-phase synthesis. The synthesis of glucuronic acid from glucose is described using an oxidation procedure not previously explored in oligosaccharide construction.</Abstract> <Access xmlns="http://purl.org/coar/access_right" > </Access> </Publication>