Date of Award

8-2019

Level of Access Assigned by Author

Open-Access Thesis

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry

Advisor

Matthew Brichacek

Second Committee Member

Barbara J.W. Cole

Third Committee Member

Alice E. Bruce

Additional Committee Members

Raymond C. Fort, Jr.

William M. Gramlich

Abstract

Glycans can be found in every living organism from plants to bacteria and viruses to human. It has been known that glycans are involved in many biological processes such as structural roles, specific recognition with glycan-binding proteins, and host-pathogen recognitions. However, the understanding of glycan structure-function relationship is limited due to the structural complexity and heterogeneity. In this work, chemical approaches have been developed to facilitate the investigation of structures and functions of glycans. A tetrazine auxiliary was synthesized and its utility in a variety of glycomic applications including purification and fractionation of complex carbohydrates, compatibility in chemoenzymatic reaction with glycosyltransferases, and direct conjugation to chemical probes was demonstrated. A new chemoselective transformation of aldehydes to nitriles was discovered and found to be useful for a variety of substrates such as reducing sugars and simple aldehydes. Furthermore, the chemical tools were applied to the chemical investigation of poly(ADP-ribose) including the functionalization of ADP-ribose with the tetrazine auxiliary and the synthesis of a photoremovable beta-NAD+ analogue.

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