1,4-Benzoquinone and 1,4-Naphthoquinone Natural Products: C-H Functionalization and Enzymatic Activity
Date Thesis Awarded
Honors Thesis -- Access Restricted On-Campus Only
Bachelors of Science (BS)
Robert J. Hinkle
Randolph A. Coleman
Quinones are organic compounds with conjugated cyclic di-ketone structures. Allyl and isoprenoid quinones are often found as bioactive natural products and are important components of the cell membranes in living organisms. In particular, we are interested in the synthesis and biochemistry of naturally occurring derivatives of ubiquinone-1 (Coenzyme Q1). To that end, the project had two major focuses.
First, the synthesis and characterization of 5-prenyl-2-methyl-1,4-benzoquinone and its analogs were achieved via direct C-H functionalization. A series of derivatives was synthesized in good yields from commercially available quinones. In addition, the characterization and structural elucidation of regioisomers was performed.
Second, the enzymatic activity for NADH:ubiquinone oxidoreductase (complex I) was assayed. Synthesized quinones were tested as potential substrates or inhibitors of the complex I from Aquifex aeolicus. 5-prenyl-2-methyl-1,4-benzoquinone was shown to function as a substrate with high enzymatic activity.
Han, Zhenyu, "1,4-Benzoquinone and 1,4-Naphthoquinone Natural Products: C-H Functionalization and Enzymatic Activity" (2019). Undergraduate Honors Theses. William & Mary. Paper 1326.
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