Dissertation/Thesis Abstract

Effect of O-4 Substituents in Sialylation Reactions and Synthesis of O-7 Substituents
by Yu, Charlene, M.S., Southern Illinois University at Edwardsville, 2017, 74; 10249954
Abstract (Summary)

Sialic acid-containing glycoconjugates are natural products with a wide variety of biological functions and therefore very important synthetic targets. Sialylation reactions to form sialic acid glycosidic bonds are still challenging. The study of O-protecting groups in the mainstream of carbohydrate chemistry occupies a very important niche and represents the major venue to control reactivity and stereocontrol of glycosyl donors. However, O-substitution of sialic acids, beyond traditional acetates, and the effect that O-substituents may have on the outcome of sialylation remains practically unknown. Recently, we showed that introduction of TBDMS and benzoyl substituents at O-4 produces very interesting and rather unpredictable sialyl donor properties. As part of a broader research project on the effect of O-protecting groups in sialic acid chemistry, herein we present the synthesis of novel sialyl donors bearing at C-4 monochloroacetyl group and testing them for the synthesis of sialic acid containing glycoconjugates. We also report the development of a methodology to selectively introduce substituents at C-7.

Indexing (document details)
Advisor: De Meo, Cristina
Commitee: Dixon, Robert, Lu, Yun, Shabestary, Nahid
School: Southern Illinois University at Edwardsville
Department: Chemistry
School Location: United States -- Illinois
Source: MAI 56/03M(E), Masters Abstracts International
Subjects: Chemistry, Organic chemistry
Publication Number: 10249954
ISBN: 978-1-369-53887-8
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