Tentative biosynthetic pathways of some microbial diketopiperazines

Gu, Bin-Bin; He, Shan; Yan, Xiaojun; Zhang, Lixin

doi:10.1007/s00253-013-5175-4

Cited by 47 publications

(45 citation statements)

References 89 publications

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“…CDPSs are generally genetically associated with cyclodipeptidetailoring enzymes in biosynthetic pathways dedicated to the synthesis of diketopiperazines 11,18 . Only five CDPS-dependent pathways have been fully characterized so far, and the incorporation of hydrophobic amino acids into cyclodipeptides and their modification by oxidation and methylation reactions have been described 8,9,17,[19][20][21] .…”

Section: Discussionmentioning

confidence: 99%

Analysis of 51 cyclodipeptide synthases reveals the basis for substrate specificity

et al. 2015

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Cyclodipeptide synthases (CDPSs) constitute a family of peptide bond-forming enzymes that use aminoacyl-tRNAs for the synthesis of cyclodipeptides. Here, we describe the activity of 41 new CDPSs. We also show that CDPSs can be classified into two main phylogenetically distinct subfamilies characterized by specific functional subsequence signatures, named NYH and XYP. All 11 previously characterized CDPSs belong to the NYH subfamily, suggesting that further special features may be yet to be discovered in the other subfamily. CDPSs synthesize a large diversity of cyclodipeptides made up of 17 proteinogenic amino acids. The identification of several CDPSs having the same specificity led us to determine specificity sequence motifs that, in combination with the phylogenetic distribution of CDPSs, provide a first step toward being able to predict the cyclodipeptides synthesized by newly discovered CDPSs. The determination of the activity of ten more CDPSs with predicted functions constitutes a first experimental validation of this predictive approach.

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Section: Discussionmentioning

confidence: 99%

Analysis of 51 cyclodipeptide synthases reveals the basis for substrate specificity

et al. 2015

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“…DKP biosynthesis by NRPSs is relatively rare, with the NRPS machineries responsible for producing such DKP producing peptides containing a specic condensation domain to catalyse the formation of the DKP ring. 231,295,296 Whilst not a biosynthetic reaction as such, the production of DKPs via spontaneous cyclisation has proved to be most useful in the in vitro characterisation of complex NRPS machineries, as it allows the initial two modules of an NRPS to be used as a standalone catalytic system without the requirement to reconstitute the entire NRPS.…”

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confidence: 99%

Unrivalled diversity: the many roles and reactions of bacterial cytochromes P450 in secondary metabolism

et al. 2018

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The cytochromes P450 (P450s) are a superfamily of heme-containing monooxygenases that perform diverse catalytic roles in many species, including bacteria. The P450 superfamily is widely known for the hydroxylation of unactivated C-H bonds, but the diversity of reactions that P450s can perform vastly exceeds this undoubtedly impressive chemical transformation. Within bacteria, P450s play important roles in many biosynthetic and biodegradative processes that span a wide range of secondary metabolite pathways and present diverse chemical transformations. In this review, we aim to provide an overview of the range of chemical transformations that P450 enzymes can catalyse within bacterial secondary metabolism, with the intention to provide an important resource to aid in understanding of the potential roles of P450 enzymes within newly identified bacterial biosynthetic pathways. 1.Introduction to P450s 2.Chemistry of P450 enzymes 3.Bacterial biosynthesis pathways involving P450s 3.1Terpene metabolism 3.1. Battersby (1925Battersby ( -2018 to the molecular understanding of biosynthesis over the course of their careers.

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“…This enzyme attaches proline to transfer RNA (tRNA), which serves as a substrate for ribosomal protein synthesis, explaining its consistent expression in control conditions in this dataset ( Figure 3B). The cyclodipeptide ring of diketopiperazines such as diproline is typically synthesized by either nonribosomal peptide synthetases (NRPS) or cyclodipeptide synthases (CDPS) 78 . Interestingly, CDPS require aminoacyl-tRNA as a substrate for the reaction instead of a free amino acid 79 .…”

Section: Responses To Sip Specific For Mt-mentioning

confidence: 99%

Mating type specific transcriptomic response to sex inducing pheromone in the pennate diatomSeminavis robusta

Bilcke

Berge

Decker

et al. 2020

Preprint

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Sexual reproduction is a fundamental phase in the life cycle of most diatoms. Despite its role as a source of genetic variation, it is rarely reported in nature and its molecular foundations remain largely unknown.Here, we integrate independent transcriptomic datasets, in order to prioritize genes responding to sex inducing pheromones (SIPs) in the pennate diatom Seminavis robusta. We observe marked gene expression changes associated with SIP treatment in both mating types, including an inhibition of S-phase progression, chloroplast division, mitosis and cell wall formation. Meanwhile, meiotic genes are upregulated in response to SIP, including a sexually induced diatom specific cyclin (dsCyc). Our data further suggest an important role for reactive oxygen species, energy metabolism and cGMP signaling during the early stages of sexual reproduction. In addition, we identify several genes with a mating type specific response to SIP, and link their expression pattern with physiological responses such as the production of the attraction pheromone diproline and mate-searching behaviour in MT+. Combined, our results provide a model for early sexual reproduction in pennate diatoms and significantly expand the suite of target genes to detect sexual reproduction events in natural diatom populations.

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Tentative biosynthetic pathways of some microbial diketopiperazines

Cited by 47 publications

References 89 publications

Analysis of 51 cyclodipeptide synthases reveals the basis for substrate specificity

Analysis of 51 cyclodipeptide synthases reveals the basis for substrate specificity

Unrivalled diversity: the many roles and reactions of bacterial cytochromes P450 in secondary metabolism

Mating type specific transcriptomic response to sex inducing pheromone in the pennate diatomSeminavis robusta

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