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SYNTHETIC STUDIES OF GLYCOPEPTIDES AND GLYCOCONJUGATES

Shao, Ning
http://rave.ohiolink.edu/etdc/view?acc_num=case1105557527

Abstract Details

2005, Doctor of Philosophy, Case Western Reserve University, Chemistry.
Glycopeptides, glycoproteins and other glycoconjugates play an important role in various physiological and pathological processes. Therefore, the demands for them from numerous studies have been constantly growing. Despite the advances made in both carbohydrate and glycopeptide chemistry, synthesis of complex glycopeptides is still a great challenge. Developing new efficient strategies and their application to the synthesis of important glycopeptides are highly desired. The solution-phase synthesis with solid-phase workup (SSSW) strategy was deliberately developed for the syntheses of glycopeptides. By using unprotected glycosyl amino acids as building blocks, this new strategy delivers glycopeptides containing no protecting groups in their sugar moieties, eliminating any side reactions involved in the deprotections, such as deacetylation and debenzylation. Moreover, the intermediates were easily isolated by precipitation, and no column chromatography was necessary until the final product was obtained. In this thesis, SSSW was used to synthesize natural N-linked and O-linked glycopeptides. An efficient synthesis of O-linked glycopeptides 2.46 and 2.49 with multiple TF antigens is first described. The O-linked glycosyl amino acids were constructed stereoselectively using a benzyl protected glycosyl fluoride donor. After removing protecting groups from the sugar moiety, the resultant glycosyl amino acids were used in the syntheses of glycopeptides by SSSW. This strategy was also applied to the synthesis of an N-linked CD52 glycopeptide 3.1, containing an acid-labile fucosyl linkage. The unprotected fucosidic bond was stable to the TFA treatment. Finally, a solid-phase synthesis of a protected CD52 glycopeptide 4.2 with the core hexasaccharide is described. An acid-sensitive 2-chlorotrityl resin was chosen as the solid-phase support to allow selective release of the glycopeptide, without affecting the acid-labile protecting groups and more importantly, the fucosidic bond. It then served as a key building block in the synthesis of CD52 antigen, a GPI anchored glycopeptide.
Zhongwu Guo (Advisor)
222 p.
glycopeptides; glycoconjugates; Solution-phase synthesis with solid-phase workup; CD52 antigen

Recommended Citations

Citations

  • Shao, N. (2005). SYNTHETIC STUDIES OF GLYCOPEPTIDES AND GLYCOCONJUGATES [Doctoral dissertation, Case Western Reserve University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=case1105557527

    APA Style (7th edition)

  • Shao, Ning. SYNTHETIC STUDIES OF GLYCOPEPTIDES AND GLYCOCONJUGATES. 2005. Case Western Reserve University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=case1105557527.

    MLA Style (8th edition)

  • Shao, Ning. "SYNTHETIC STUDIES OF GLYCOPEPTIDES AND GLYCOCONJUGATES." Doctoral dissertation, Case Western Reserve University, 2005. http://rave.ohiolink.edu/etdc/view?acc_num=case1105557527

    Chicago Manual of Style (17th edition)

case1105557527
1,877
© 2005, all rights reserved.
This open access ETD is published by Case Western Reserve University School of Graduate Studies and OhioLINK.