Bisucaberin biosynthesis: an adenylating domain of the BibC multi-enzyme catalyzes cyclodimerization of N-hydroxy-N-succinylcadaverine

Kadi, Nadia; Song, Lijiang; Challis, Gregory L.

doi:10.1039/b813029a

Cited by 52 publications

(72 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Identity of the genomic biosynthetic gene cluster for the 1,3‐diaminopropane‐based siderophore rhizobactin 1021 has been genetically confirmed in S. meliloti (Lynch et al ., ). Biosynthetic gene clusters for the cadaverine‐based siderophores desferrioxamine E (Barona‐Gomez et al ., ) and bisucabin (Kadi et al ., ) have been confirmed biochemically. We analysed bacterial and archaeal genomes for the presence of NIS‐type biosynthetic gene clusters containing either a DABA DC homologue in the absence of an adjacent DABA AT (i.e.…”

Section: Resultsmentioning

confidence: 99%

“…This pathway produces structurally diverse siderophores including a number of hydroxamate group‐containing molecules for which the corresponding biosynthetic gene clusters have been identified (Fig. ), including aerobactin (de Lorenzo et al ., ), rhizobactin 1021 (Lynch et al ., ), putrebactin (Kadi et al ., ), bisucaberin (Kadi et al ., ) and desferrioxamine E (Barona‐Gomez et al ., ). Similar siderophore structures (Fig.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Evolution of a novel lysine decarboxylase in siderophore biosynthesis

Burrell

Hanfrey

Kinch

et al. 2012

Molecular Microbiology

View full text Add to dashboard Cite

SummaryStructural backbones of iron-scavenging siderophore molecules include polyamines 1,3-diaminopropane and 1,5-diaminopentane (cadaverine). For the cadaverine-based desferroxiamine E siderophore in Streptomyces coelicolor, the corresponding biosynthetic gene cluster contains an ORF encoded by desA that was suspected of producing the cadaverine (decarboxylated lysine) backbone. However, desA encodes an L-2,4-diaminobutyrate decarboxylase (DABA DC) homologue and not any known form of lysine decarboxylase (LDC). The only known function of DABA DC is, together with L-2,4-aminobutyrate aminotransferase (DABA AT), to synthesize 1,3-diaminopropane. We show here that S. coelicolor desA encodes a novel LDC and we hypothesized that DABA DC homologues present in siderophore biosynthetic clusters in the absence of DABA AT ORFs would be novel LDCs. We confirmed this by correctly predicting the LDC activity of a DABA DC homologue from a Yersinia pestis siderophore biosynthetic pathway. The corollary was confirmed for a DABA DC homologue, adjacent to a DABA AT ORF in a siderophore pathway in the cyanobacterium Anabaena variabilis, which was shown to be a bona fide DABA DC. These findings enable prediction of whether a siderophore pathway will utilize 1,3-diaminopropane or cadaverine, and suggest that the majority of bacteria use DABA AT and DABA DC for siderophore, rather than norspermidine/ polyamine biosynthesis.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Evolution of a novel lysine decarboxylase in siderophore biosynthesis

Burrell

Hanfrey

Kinch

et al. 2012

Molecular Microbiology

View full text Add to dashboard Cite

show abstract

“…This apparent lack of sensitivity might be expected for the virtually identical chemical transformations involved (Fig. 2C), [11, 12] especially in light of an earlier study showing that the AvbD homolog PubC catalyses both dimerization and cyclization. [11] …”

mentioning

confidence: 93%

“…algae B516 and found only a single gene cluster with homology to the bisucaberin and putrebactin clusters, which have been described previously for other species (Figure 2A, Figure S14). [11, 12] This cluster, ( avbA - D ), had highest homologies with genes in the bisucaberin cluster bibA - C of Vibrio salmonicida [12] or genes in the putrebactin cluster pubA - C of Shewanella putrefaciens (Table S2). [11] …”

mentioning

confidence: 99%

See 1 more Smart Citation

A Chimeric Siderophore Halts Swarming Vibrio

Böttcher

Clardy

2014

Angew Chem Int Ed

View full text Add to dashboard Cite

Some bacteria under some circumstances swarm; they move rapidly and collectively over a surface. In an effort to understand the molecular signals controlling swarming, we isolated two strains from the same red seaweed – Vibrio alginolyticus B522, a vigorous swarmer, and Shewanella algae B516, which inhibits V. alginolyticus swarming in its vicinity. Plate assays combined with NMR, MS, and X-ray diffraction analyses identified a small molecule, which was named avaroferrin, as a potent swarming inhibitor. Avaroferrin, a previously unreported cyclic dihydroxamate siderophore, is a chimera of two well-known siderophores: putrebactin and bisucaberin. The sequenced genome of S. algae revealed avaroferrin’s biosynthetic gene cluster to be a mashup of putrebactin and bisucaberin biosynthetic genes. Avaroferrin blocks swarming through its ability to bind iron in a form that cannot be pirated by V. alginolyticus, thereby securing this essential resource for its producer.

show abstract

Ein chimärer Siderophor stoppt das Schwarmverhalten von Vibrio

Böttcher

Clardy

2014

Angewandte Chemie

View full text Add to dashboard Cite

Unter bestimmten Bedingungen beginnen manche Bakterien zu schwärmen; sie bewegen sich rasch und als Kollektiv über eine Oberfläche. Um die molekularen Signalstoffe, die das Schwarmverhalten kontrollieren, besser zu verstehen, isolierten wir zwei Bakterienstämme von einer RotalgenprobeVibrio alginolyticus B522, ein aktiv schwärmender Stamm, und Shewanella algae B516, der das Schwärmen von V. alginolyticus in seinem Umfeld inhibiert. (Abbildung 1 A). Dieses Isolat wurde durch phylogenetische Analyse der 16S-RNA und der gyrBGensequenz als Shewanella algae identifiziert (Abbildung S1 in den Hintergrundinformationen).Hochauflçsende Differentialinterferenzkontrast(DIC)-Mikroskopie zeigte, dass die klare Zone nicht durch einen antibiotischen Effekt zustande kam, da sich auch innerhalb der Zone eine dünne Schicht lebender, aber nicht mobiler Zellen von V. alginolyticus fand. Mit DIC-Aufnahmen im Zeitraffer konnten wir zeigen, dass die Beweglichkeit der Zellen in der Inhibitionszone (S1) stark eingeschränkt war im Vergleich zu außerhalb (S2) oder verglichen mit den Negativkontrollen (C1 und C2) in gleichem Abstand (Abbildung 1 B, Abbildung S2). Längere Inkubationszeiten (mehrere Tage) führten zum Verschwinden der Zone, was uns schlussfolgern ließ, dass lediglich die Mobilität von V. alginolyticus B522 durch S. algae verringert wurde. Unsere computergestützte Analyse der mikroskopischen Zeitrafferaufnahmen bestätigte die visuellen Beobachtungen, und Zellen in der Inhibitonszone verbrachten signifikant weniger Zeit in Bewegung (Abbildung S3

show abstract

Bisucaberin biosynthesis: an adenylating domain of the BibC multi-enzyme catalyzes cyclodimerization of N-hydroxy-N-succinylcadaverine

Abstract: The bisucaberin biosynthetic gene cluster has been identified in Vibrio salmonicida and a domain from within the BibC multienzyme encoded by the cluster has been shown to catalyse ATP-dependent dimerisation and macrocyclisation of N-hydroxy-N-succinylcadaverine to form bisucaberin.

Cited by 52 publications

References 23 publications

Evolution of a novel lysine decarboxylase in siderophore biosynthesis

Evolution of a novel lysine decarboxylase in siderophore biosynthesis

A Chimeric Siderophore Halts Swarming Vibrio

Ein chimärer Siderophor stoppt das Schwarmverhalten von Vibrio

Contact Info

Product

Resources

About