Date of Award




Document Type


Degree Name

Doctor of Philosophy (PhD)


Department of Chemistry

Content Description

1 online resource (xv, 263 pages) : illustrations (some color)

Dissertation/Thesis Chair

Qiang QZ Zhang

Committee Members

Ting TW Wang, Pan PL Li, Jeremy JF Feldblyum, Maksim MR Royzen


dimer, NCL, reversible, Dimerization, Organic compounds, Lactones

Subject Categories

Organic Chemistry


Chapter 1: Dimers of naphthalenol derivatives were synthesized by photocatalysis, cobalt(II) acetylacetonate. Several functional groups were tolerant of its skeleton. This novel dimer was connected through a reversible sigma bond. Its reversibility was confirmed by chiral HPLC and 1H-NMR experiments. Through EPR and Stern-Volmer quenching experiments, we proposed the reaction mechanism. The reversibility property can be potentially beneficial in polymers, self-healing, and memory materials.Chapter 2: We report an epimerization-free native chemical ligation reaction by β-lactone-mediated peptides. This approach can achieve Thr-Xaa efficiently and rapidly. Besides, it has a broad side-chain tolerance. Through the competition reaction experiment, it was demonstrated that thiol played a crucial role in the native chemical ligation reaction. Under optimized conditions, it was shown to be capable of synthesizing thioester, which cannot be generated directly by solid-phase peptide synthesis. Two unnatural cyclic peptides were also synthesized by this method.