2018
DOI: 10.1021/jacs.8b05354
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Discovery of Unprecedented Hydrazine-Forming Machinery in Bacteria

Abstract: Recent studies described several different routes that facilitate nitrogen-nitrogen bond formation in natural product biosynthesis. We report herein the identification of unprecedented machinery for hydrazine formation involved in the biosynthesis of s56-p1, a dipeptide natural product with a unique hydrazone unit. The gene cassette comprising this machinery is widespread across several bacterial phyla, highlighting the overlooked potential of bacteria to synthesize hydrazine.

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Cited by 70 publications
(148 citation statements)
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“…As an example, N5 of ornithine is hydroxylated by a flavin‐dependent enzyme (KtzI) before N−N bond formation promoted by a heme enzyme (KtzT, Figure S1 in the Supporting Information) . Similarly, N 6 ‐hydroxylysine is conjugated to glycine followed by intramolecular nucleophilic attack from the glycine amino group catalyzed by a fusion protein (Spb40) consisting of a cupin and a methionyl‐tRNA synthetase‐like protein (Figure S1) …”
Section: Figurementioning
confidence: 99%
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“…As an example, N5 of ornithine is hydroxylated by a flavin‐dependent enzyme (KtzI) before N−N bond formation promoted by a heme enzyme (KtzT, Figure S1 in the Supporting Information) . Similarly, N 6 ‐hydroxylysine is conjugated to glycine followed by intramolecular nucleophilic attack from the glycine amino group catalyzed by a fusion protein (Spb40) consisting of a cupin and a methionyl‐tRNA synthetase‐like protein (Figure S1) …”
Section: Figurementioning
confidence: 99%
“…It is notable that tri26–31 are homologous to the gene cassette spb38–43 , which was found to be essential for the biosynthesis of the glyoxylate hydrazine unit in s56‐p1 . This thus suggests that, in a triacsin, at least one N−N bond is formed through the action of Tri28, the homologue of Spb40 consisting of a cupin and a methionyl‐tRNA synthetase‐like protein.…”
Section: Figurementioning
confidence: 99%
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“…[35] Enzymes encoded by the latter set of genes have been shown to catalyze the transformation of lysine and glycine to give hydrazino acetic acid (20) enroute to s56-p1 (Scheme 2B). [35] Hence,h ydrazine formation may also be involved in the construction of the pyrazole group of formycins [33] and perhaps pyrazofurin as well (Scheme 2C). If correct, this hypothesis suggested acriterion by which the pyrazofurin gene cluster might be identified in ag enome-wide search of the producing strain.…”
mentioning
confidence: 99%
“…B Formationo fhydrazino acetic acid (20) in the biosynthesis of s56-p1 (21). [35] C Possible involvement of ForJ/K/ La nd PyfG/H/I in hydrazine assembly in formycin and pyrazofurin biosynthesis,respectively. bioinformatic analysis collectively suggested that the pyf cluster encodes the enzymes of pyrazofurin biosynthesis.…”
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confidence: 99%