2026-09-20T17:13:24Zhttps://dspace.mit.edu/server/oai/requestoai:dspace.mit.edu:1721.1/178272022-01-13T07:54:21Zcom_1721.1_7582com_1721.1_7581col_1721.1_131022
Peter H. Seeberger.
Love, Kerry Routenberg, 1977-
Massachusetts Institute of Technology. Dept. of Chemistry.
Massachusetts Institute of Technology. Department of Chemistry
2005-06-02T18:49:50Z
2005-06-02T18:49:50Z
2004
2004
http://hdl.handle.net/1721.1/17827
56565295
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2004.
Vita.
Includes bibliographical references.
Cell-surface carbohydrates are markers of specific cell types. These oligosaccharides are involved in recognition, adhesion, and signal transduction events. Advances in molecular glycobiology rely heavily on straightforward access to structurally defined oligosaccharides, but traditional syntheses of complex carbohydrates have been very laborious. Development of a novel linker and monitoring of each glycosylation reaction during automated solid-phase oligosaccharide synthesis allowed for the rapid synthesis of three Lewis-type cell surface oligosaccharides. The assembly of the nonasaccharide adenocarcinoma marker Le[superscript]y-Le[superscript]x monosaccharide building blocks was achieved in just 23 hours, while the syntheses of the tumor markers Lewis X, a pentasaccharide, and Lewis Y, a hexasaccharide, required only 12 and 14 hours respectively. The automation of carbohydrate synthesis greatly accelerates access to molecules for biological study and vaccine development.
by Kerry Routenberg Love.
Ph.D.
323 p.
16531218 bytes
16568777 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.
Automated synthesis of the Lewis blood group oligosaccharides
Thesis
application/pdf
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Publication
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<Abstract>Cell-surface carbohydrates are markers of specific cell types. These oligosaccharides are involved in recognition, adhesion, and signal transduction events. Advances in molecular glycobiology rely heavily on straightforward access to structurally defined oligosaccharides, but traditional syntheses of complex carbohydrates have been very laborious. Development of a novel linker and monitoring of each glycosylation reaction during automated solid-phase oligosaccharide synthesis allowed for the rapid synthesis of three Lewis-type cell surface oligosaccharides. The assembly of the nonasaccharide adenocarcinoma marker Le[superscript]y-Le[superscript]x monosaccharide building blocks was achieved in just 23 hours, while the syntheses of the tumor markers Lewis X, a pentasaccharide, and Lewis Y, a hexasaccharide, required only 12 and 14 hours respectively. The automation of carbohydrate synthesis greatly accelerates access to molecules for biological study and vaccine development.</Abstract>
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