New Catalytic Motifs in Flavoenzymology

Adak, Sanjoy; Jhulki, Isita; Begley, Tadhg P.

doi:10.1016/b978-0-12-409547-2.14836-x

Comprehensive Natural Products III 2020

DOI: 10.1016/b978-0-12-409547-2.14836-x

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New Catalytic Motifs in Flavoenzymology

Sanjoy Adak¹,

Isita Jhulki²,

Tadhg P. Begley³

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2023

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Cited by 1 publication

(2 citation statements)

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“…In this report, we propose the C–S bond cleavage step proceeds via an oxathiiranium intermediate 37. This discovery adds yet another example to the growing number of new flavin catalytic motifs discovered over the past 20 years. − …”

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confidence: 88%

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Alkylcysteine Sulfoxide C–S Monooxygenase Uses a Flavin-Dependent Pummerer Rearrangement

Hazra

Begley

2023

J. Am. Chem. Soc.

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Flavoenzymes are highly versatile and participate in the catalysis of a wide range of reactions, including key reactions in the metabolism of sulfur-containing compounds. S-Alkyl cysteine is formed primarily by the degradation of S-alkyl glutathione generated during electrophile detoxification. A recently discovered S-alkyl cysteine salvage pathway uses two flavoenzymes (CmoO and CmoJ) to dealkylate this metabolite in soil bacteria. CmoO catalyzes a stereospecific sulfoxidation, and CmoJ catalyzes the cleavage of one of the sulfoxide C–S bonds in a new reaction of unknown mechanism. In this paper, we investigate the mechanism of CmoJ. We provide experimental evidence that eliminates carbanion and radical intermediates and conclude that the reaction proceeds via an unprecedented enzyme-mediated modified Pummerer rearrangement. The elucidation of the mechanism of CmoJ adds a new motif to the flavoenzymology of sulfur-containing natural products and demonstrates a new strategy for the enzyme-catalyzed cleavage of C–S bonds.

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confidence: 88%

“…This discovery adds yet another example to the growing number of new flavin catalytic motifs discovered over the past 20 years. 44 − 53 …”

mentioning

confidence: 99%

Alkylcysteine Sulfoxide C–S Monooxygenase Uses a Flavin-Dependent Pummerer Rearrangement

Hazra

Begley

2023

J. Am. Chem. Soc.

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New Catalytic Motifs in Flavoenzymology

Cited by 1 publication

References 97 publications

Alkylcysteine Sulfoxide C–S Monooxygenase Uses a Flavin-Dependent Pummerer Rearrangement

Alkylcysteine Sulfoxide C–S Monooxygenase Uses a Flavin-Dependent Pummerer Rearrangement

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