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Oxidative cyclization of prodigiosin by an alkylglycerol monooxygenase-like enzyme.

ABSTRACT: Prodiginines, which are tripyrrole alkaloids displaying a wide array of bioactivities, occur as linear and cyclic congeners. Identification of an unclustered biosynthetic gene led to the discovery of the enzyme responsible for catalyzing the regiospecific C-H activation and cyclization of prodigiosin to cycloprodigiosin in Pseudoalteromonas rubra. This enzyme is related to alkylglycerol monooxygenase and unrelated to RedG, the Rieske oxygenase that produces cyclized prodiginines in Streptomyces, implying convergent evolution.

SUBMITTER: de Rond T

PROVIDER: S-EPMC5677514 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature

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Oxidative cyclization of prodigiosin by an alkylglycerol monooxygenase-like enzyme.

de Rond Tristan T Stow Parker P Eigl Ian I Johnson Rebecca E RE Chan Leanne Jade G LJG Goyal Garima G Baidoo Edward E K EEK Hillson Nathan J NJ Petzold Christopher J CJ Sarpong Richmond R Keasling Jay D JD

Nature chemical biology 20170911 11

Prodiginines, which are tripyrrole alkaloids displaying a wide array of bioactivities, occur as linear and cyclic congeners. Identification of an unclustered biosynthetic gene led to the discovery of the enzyme responsible for catalyzing the regiospecific C-H activation and cyclization of prodigiosin to cycloprodigiosin in Pseudoalteromonas rubra. This enzyme is related to alkylglycerol monooxygenase and unrelated to RedG, the Rieske oxygenase that produces cyclized prodiginines in Streptomyces, ...[more]

PMID: 28892091

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