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

Author(s): Cooper S. Jamieson ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Masao Ohashi ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Fang Liu ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Yi Tang ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , K. N. Houk ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵

Publication date (Electronic): 2019

Journal: Natural Product Reports

Publisher: Royal Society of Chemistry (RSC)

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Abstract

The pericyclases are Nature's route to spirotetronates, statins, myceliothermophins, leporins and more.

Abstract

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.

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Assembly-line enzymology for polyketide and nonribosomal Peptide antibiotics: logic, machinery, and mechanisms.

Michael A. Fischbach, Christopher Walsh (2006)

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Computational design of an enzyme catalyst for a stereoselective bimolecular Diels-Alder reaction.

Justin B. Siegel, Alexandre Zanghellini, Helena M. Lovick … (2010)

The Diels-Alder reaction is a cornerstone in organic synthesis, forming two carbon-carbon bonds and up to four new stereogenic centers in one step. No naturally occurring enzymes have been shown to catalyze bimolecular Diels-Alder reactions. We describe the de novo computational design and experimental characterization of enzymes catalyzing a bimolecular Diels-Alder reaction with high stereoselectivity and substrate specificity. X-ray crystallography confirms that the structure matches the design for the most active of the enzymes, and binding site substitutions reprogram the substrate specificity. Designed stereoselective catalysts for carbon-carbon bond-forming reactions should be broadly useful in synthetic chemistry.