Issue 8, 2018

Roles of 2-oxoglutarate oxygenases and isopenicillin N synthase in β-lactam biosynthesis

Abstract

Covering: up to 2017

2-Oxoglutarate (2OG) dependent oxygenases and the homologous oxidase isopenicillin N synthase (IPNS) play crucial roles in the biosynthesis of β-lactam ring containing natural products. IPNS catalyses formation of the bicyclic penicillin nucleus from a tripeptide. 2OG oxygenases catalyse reactions that diversify the chemistry of β-lactams formed by both IPNS and non-oxidative enzymes. Reactions catalysed by the 2OG oxygenases of β-lactam biosynthesis not only involve their typical hydroxylation reactions, but also desaturation, epimerisation, rearrangement, and ring-forming reactions. Some of the enzymes involved in β-lactam biosynthesis exhibit remarkable substrate and product selectivities. We review the roles of 2OG oxygenases and IPNS in β-lactam biosynthesis, highlighting opportunities for application of knowledge of their roles, structures, and mechanisms.

Graphical abstract: Roles of 2-oxoglutarate oxygenases and isopenicillin N synthase in β-lactam biosynthesis

Article information

Article type
Review Article
Submitted
09 Jan 2018
First published
29 May 2018
This article is Open Access
Creative Commons BY license

Nat. Prod. Rep., 2018,35, 735-756

Roles of 2-oxoglutarate oxygenases and isopenicillin N synthase in β-lactam biosynthesis

P. Rabe, J. J. A. G. Kamps, C. J. Schofield and C. T. Lohans, Nat. Prod. Rep., 2018, 35, 735 DOI: 10.1039/C8NP00002F

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