Attempts towards Total Synthesis of Photocaged Nicotinamide Adenine Dinucleotide (NAD+) and Its Analogues

Doctoral Dissertation
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Abstract

Understanding the mechanism of enzymes has a paramount role in drug discovery and chemical biology. To reach these goals, it is necessary to have access to chemical tools, which improve our understanding about the biochemical pathways. In this thesis, the synthesis of photocaged nicotinamide using p-hydroxyphenacyl as the caging group has been accomplished and the photophysical and photolytic properties were established. NAD+ as a redox cofactor plays a pivotal role in metabolism. Different strategies for the synthesis of NAD+ and its analog were explored by applying the Zincke reaction and the addition of organozinc reagents. The synthesis of the NMN moiety of 4-alkyl NAD+ was successfully developed by chemoselective addition of organozinc reagents. Finally, palladium catalyzes the asymmetric conjugation addition to cyclic enones for generating quaternary carbon centers using novel chiral pyridine-oxazolines ligands, which were explored to experimentally test computational predictions of stereoselectivity.

Attributes

Attribute NameValues
Author Farbod Salahi
Contributor Olaf G. Wiest, Research Director
Contributor Paul Helquist, Research Director
Degree Level Doctoral Dissertation
Degree Discipline Chemistry and Biochemistry
Degree Name Doctor of Philosophy
Banner Code
  • PHD-CHEM

Defense Date
  • 2019-08-01

Submission Date 2019-10-02
Record Visibility and Access Public
Content License
  • All rights reserved

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