Automated synthesis of the Lewis blood group oligosaccharides
Name
56565295-MIT.pdf
Description
Full printable version
Size
15.8 MB
Format
Adobe PDF
Checksum (MD5)
2191a6a0d5c217c50dc82c794b84fa8b
Author(s)
Love, Kerry Routenberg, 1977-
Advisor(s)
Peter H. Seeberger.
Date Issued
2004
Publisher
Massachusetts Institute of Technology
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.
Description
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2004.
Vita.
Includes bibliographical references.
Subjects
Chemistry.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
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