Initiation of the flexirubin biosynthesis in <scp><i>C</i></scp><i>hitinophaga pinensis</i>

Schöner, Tim A.; Fuchs, Sebastian W.; Schönau, Christian; Bode, Helge B.

doi:10.1111/1751-7915.12110

Cited by 41 publications

(44 citation statements)

References 30 publications

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“…Our labeling result with 4F-3HBA now confirms that this is indeed the case in the biosynthesis of pigment 8 from Azoarcus which additionally contains a methionine derived methylgroup. Furthermore the MS 3 of the assigned polyene fragment m/z 317.2 shows mass shifts of Δ28 Da (CO), Δ78 Da (C 6 H 6 ) or Δ26 Da (C 2 H 2 ) (Figure S2.C), already known from mass spectrometric fragmentation of flexirubin-like polyenes [31], [35]. These results suggest the structure of a nonbrominated aryl-heptaene for the polyene moiety of 8 , reflecting xanthomonadin group-11 previously found in Xanthomonas [36], [37].…”

Section: Discussionmentioning

confidence: 92%

Identification and Biosynthesis of a Novel Xanthomonadin-Dialkylresorcinol-Hybrid from Azoarcus sp. BH72

et al. 2014

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A novel xanthomonadin-dialkylresorcinol hybrid named arcuflavin was identified in Azoarcus sp. BH72 by a combination of feeding experiments, HPLC-MS and MALDI-MS and gene clusters encoding the biosynthesis of this non-isoprenoid aryl-polyene containing pigment are reported. A chorismate-utilizing enzyme from the XanB2-type producing 3- and 4-hydroxybenzoic acid and an AMP-ligase encoded by these gene clusters were characterized, that might perform the first two steps of the polyene biosynthesis. Furthermore, a detailed analysis of the already known or novel biosynthesis gene clusters involved in the biosynthesis of polyene containing pigments like arcuflavin, flexirubin and xanthomonadin revealed the presence of similar gene clusters in a wide range of bacterial taxa, suggesting that polyene and polyene-dialkylresorcinol pigments are more widespread than previously realized.

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Section: Discussionmentioning

confidence: 92%

Identification and Biosynthesis of a Novel Xanthomonadin-Dialkylresorcinol-Hybrid from Azoarcus sp. BH72

et al. 2014

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“…[342–348] On the other hand, phenylalanine and tyrosine aminomutase (PAM and TAM) catalyze the conversion of phenylalanine and tyrosine to their corresponding β-amino acids (Figure 87a). [349–352] Each of the enzymes described above contains 5-methylene-3,5-dihydroimidazole-4-one (MIO, 338 ) as a cofactor, which is formed in a spontaneous post-translational modification process involving cyclization of the backbone tripeptide Ala-Ser-Gly ( 337 )(Figure 87b).…”

Section: Miscellaneousmentioning

confidence: 99%

The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems

2017

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Chemical reactions that are named in honor of their true or at least perceived discoverers are known as “name reactions”. This review is a collection of biological representatives of named chemical reactions. Emphasis is placed on reaction types and catalytic mechanisms that showcase both the chemical diversity in natural product biosynthesis as well as the parallels with synthetic organic chemistry. An attempt has been made to describe the enzymatic mechanisms of catalysis within the context of their synthetic counterparts whenever possible and to discuss the mechanistic hypotheses for those reactions that are presently active areas of investigation. This review has been categorized by reaction type, e.g., condensation, nucleophilic addition, reduction and oxidation, substitution, carboxylation, radical-mediated, and rearrangements, which are subdivided by named reactions.

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“…CHD derivatives are known as natural products for 10 y (21) and have originally been described as pollinator attractant of Chiloglottis orchids as well as sex pheromones of its pollinator, the thynnine wasp Neozeleboria cryptoides (22). DAR derivatives have been described as antibiotics (10,23), cytotoxins (24), free radical scavengers (25), and growth-stimulating factors (26) and can also be part of flexirubins and related pigments (12,27,28), which might be involved in protection against lipid peroxidation and photooxidative damage (29). Thus, especially in bacteria without LuxR homologs, DARs and CHDs might have additional functions other than acting as signals.…”

Section: Discussionmentioning

confidence: 99%

Dialkylresorcinols as bacterial signaling molecules

Brameyer

Kresovic

Bode

et al. 2014

Proc. Natl. Acad. Sci. U.S.A.

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It is well recognized that bacteria communicate via small diffusible molecules, a process termed quorum sensing. The best understood quorum sensing systems are those that use acylated homoserine lactones (AHLs) for communication. The prototype of those systems consists of a LuxI-like AHL synthase and a cognate LuxR receptor that detects the signal. However, many proteobacteria possess LuxR receptors, yet lack any LuxI-type synthase, and thus these receptors are referred to as LuxR orphans or solos. In addition to the wellknown AHLs, little is known about the signaling molecules that are sensed by LuxR solos. Here, we describe a novel cell-cell communication system in the insect and human pathogen Photorhabdus asymbiotica. We identified the LuxR homolog PauR to sense dialkylresorcinols (DARs) and cyclohexanediones (CHDs) instead of AHLs as signals. The DarABC synthesis pathway produces the molecules, and the entire system emerged as important for virulence. Moreover, we have analyzed more than 90 different Photorhabdus strains by HPLC/MS and showed that these DARs and CHDs are specific to the human pathogen P. asymbiotica. On the basis of genomic evidence, 116 other bacterial species are putative DAR producers, among them many human pathogens. Therefore, we discuss the possibility of DARs as novel and widespread bacterial signaling molecules and show that bacterial cell-cell communication goes far beyond AHL signaling in nature.

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Initiation of the flexirubin biosynthesis in Chitinophaga pinensis

Cited by 41 publications

References 30 publications

Identification and Biosynthesis of a Novel Xanthomonadin-Dialkylresorcinol-Hybrid from Azoarcus sp. BH72

Identification and Biosynthesis of a Novel Xanthomonadin-Dialkylresorcinol-Hybrid from Azoarcus sp. BH72

The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems

Dialkylresorcinols as bacterial signaling molecules

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