The expanding world of biosynthetic pericyclases: cooperation of experiment and theory for discovery

Covering: 2000 to 2018 Pericyclic reactions are a distinct class of reactions that have wide synthetic utility. Before the recent discoveries described in this review, enzyme-catalyzed pericyclic reactions were not widely known to be involved in biosynthesis. This situation is changing rapidly. We d...

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Published inNatural product reports Vol. 36; no. 5; pp. 698 - 713
Main Authors Jamieson, Cooper S, Ohashi, Masao, Liu, Fang, Tang, Yi, Houk, K. N
Format Journal Article
LanguageEnglish
Published England 22.05.2019
Subjects
Bacterial Proteins - chemistry
Bacterial Proteins - metabolism
biosynthesis
Catalysis
catalytic activity
chemical reactions
Cyclization
enzymes
Enzymes - chemistry
Enzymes - metabolism
Naphthalenes - chemistry
Naphthalenes - metabolism
Protein Conformation
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Summary:Covering: 2000 to 2018 Pericyclic reactions are a distinct class of reactions that have wide synthetic utility. Before the recent discoveries described in this review, enzyme-catalyzed pericyclic reactions were not widely known to be involved in biosynthesis. This situation is changing rapidly. We define the scope of pericyclic reactions, give a historical account of their discoveries as biosynthetic reactions, and provide evidence that there are many enzymes in nature that catalyze pericyclic reactions. These enzymes, the "pericyclases," are the subject of this review. The pericyclases are Nature's route to spirotetronates, statins, myceliothermophins, leporins and more.
Bibliography:Masao Ohashi was born in 1986 in Ibaraki, Japan. He received his Ph.D. in 2015 in Medicinal Chemistry from Okayama University, Japan. From 2015 to 2016, he joined the Department of Pharmaceutical Sciences at the University of Shizuoka as a designated assistant professor. In 2016, he joined Prof. Yi Tang's lab at the University of California, Los Angeles, as a postdoctoral scholar. His current research interests focus on the identification of new enzymes that catalyze unusual reactions, such as pericyclic reactions, in nature.
Kendall N. Houk received his PhD at Harvard with R. B. Woodward in 1968, for experimental work on pericyclic reactions. He was at Louisiana State University, the University of Pittsburgh, and the National Science Foundation before joining the University of California Los Angeles (UCLA) where he is the Saul Winstein Chair in Organic Chemistry. He is a Fellow of the American Academy of Arts and Sciences and a Member of the US National Academy of Sciences and the International Academy of Quantum Molecular Sciences.
Yi Tang received his undergraduate degree in Chemical Engineering and Material Science from Penn State University. He received his Ph.D. in Chemical Engineering from California Institute of Technology in 2002. After NIH postdoctoral training in Chemical Biology at Stanford University, he started his independent career at the University of California Los Angeles in 2004. He is currently the Chancellor Professor in the Department of Chemical and Biomolecular Engineering at UCLA, and holds joint appointments in the Department of Chemistry and Biochemistry; and Department of Bioengineering. His lab is interested in natural product biosynthesis, biocatalysis and protein engineering.
Cooper S. Jamieson was born in New York, New York and raised in San Luis Obispo, CA. In 2016, he received a B.A. in Chemistry and a B.A. in Art from Lewis & Clark College in Portland, OR. Cooper worked in art conservation at the Chinati Foundation in far-West Marfa, Texas before beginning a PhD under the direction of K. N. Houk and Y. Tang at UCLA.
Fang Liu received her B.S. in Chemistry from Nankai University, China, in 2009 and her Ph.D. with K. N. Houk at UCLA in 2014, from studying gating in container molecules and the factors controlling reactivity in bioorthogonal cycloadditions. She continued as a postdoctoral fellow in the Houk group at UCLA and the Liang group at Nanjing University. She is a Professor at Nanjing Agricultural University and principal designer/artist of DesignOne, a scientific design studio.
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ISSN:0265-0568
1460-4752
1460-4752
DOI:10.1039/c8np00075a