Nonproteinogenic Amino Acid Building Blocks for Nonribosomal Peptide and Hybrid Polyketide Scaffolds

Walsh, Christopher T.; O’Brien, Robert V.; Khosla, Chaitan

doi:10.1002/anie.201208344

Cited by 354 publications

(268 citation statements)

References 241 publications

(249 reference statements)

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“…This AMPs found from bacteria and fungi are classified as ribosomal peptide and nonribosomal peptide (NRP) according their biosynthesis. The structure of component B contains Hmp (2-hydroxy-3-methylpentanoic acid), Aba (dehydroamino acid), and Vol (valinol) which are noncanonical amino acid that frequently appeared in the NRPs (Walsh et al 2013). The character of heat-stable, adaptable to a broad pH range, and UV-resistant also indicate that component B is a typical NRP.…”

Section: Discussionmentioning

confidence: 98%

Antifungal activity of Brevibacillus laterosporus JX-5 and characterization of its antifungal components

Jiang

Wang

Xiao

et al. 2015

World J Microbiol Biotechnol

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The establishment of safe and effective methods for controlling fungal disease is an urgent issue in agriculture and forestry. Microbiological control of plant disease is expected to achieve better results than use of chemically derived fungicides. This study aimed to establish Brevibacillus laterosporus JX-5 as a potential microbiological control agent of poplar canker. The bacterium was isolated from the poplar rhizosphere and demonstrated significant growth inhibition of several pathogenic fungi in vitro. The antifungal components of Br. laterosporus JX-5 were isolated and identified. The fermentation broth of Br. laterosporus JX-5 and its main antifungal component, designated as component B, reduced Botryosphaeria dothidea associated canker of the excised poplar branch by 70 and 90%, respectively. Component B is considerably heat-stable, adaptable to a broad pH range, and UV-resistant. It could inhibit Bo. dothidea by permeating the fungal membrane, fracturing the nuclei, damaging the cell wall, and eventually killing the pathogenic fungus. The antifungal activity exhibited by Br. laterosporus JX-5 and its bioactive metabolic products indicate its feasibility as a potential biocontrol agent for plant diseases.

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Section: Discussionmentioning

confidence: 98%

Antifungal activity of Brevibacillus laterosporus JX-5 and characterization of its antifungal components

Jiang

Wang

Xiao

et al. 2015

World J Microbiol Biotechnol

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“…Nonribosomal peptides are a structurally and functionally privileged class of natural products constructed from a highly diverse pool of potential proteinogenic and nonproteinogenic amino acid building blocks (Walsh et al, 2013; Walsh, 2016). Members of the family include well-known pharmacologically relevant agents, such as vancomycin, daptomycin, penicillin, cyclosprin, and many others.…”

Section: Introductionmentioning

confidence: 99%

Genome mining unearths a hybrid nonribosomal peptide synthetase-like-pteridine synthase biosynthetic gene cluster

Park

Perez

Barber

et al. 2017

eLife

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Nonribosomal peptides represent a large class of metabolites with pharmaceutical relevance. Pteridines, such as pterins, folates, and flavins, are heterocyclic metabolites that often serve as redox-active cofactors. The biosynthetic machineries for construction of these distinct classes of small molecules operate independently in the cell. Here, we discovered an unprecedented nonribosomal peptide synthetase-like-pteridine synthase hybrid biosynthetic gene cluster in Photorhabdus luminescens using genome synteny analysis. P. luminescens is a Gammaproteobacterium that undergoes phenotypic variation and can have both pathogenic and mutualistic roles. Through extensive gene deletion, pathway-targeted molecular networking, quantitative proteomic analysis, and NMR, we show that the genetic locus affects the regulation of quorum sensing and secondary metabolic enzymes and encodes new pteridine metabolites functionalized with cis-amide acyl-side chains, termed pepteridine A (1) and B (2). The pepteridines are produced in the pathogenic phenotypic variant and represent the first reported metabolites to be synthesized by a hybrid NRPS-pteridine pathway. These studies expand our view of the combinatorial biosynthetic potential available in bacteria.DOI: http://dx.doi.org/10.7554/eLife.25229.001

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“…20). 215 Furthermore, modied amino acids such as b-hydroxy amino acids have been identied in a number of non-ribosomal peptides, including the vancomycin-type antibiotics (Tyr), 216-219 the aminocoumarincontaining angucycline antibiotics (Tyr; novobiocin, simocyclinone, coumermycin, clorobiocin), 220 echinomycin (plus other compounds that contain the intercalative chromophores quinoxaline-2-carboxylic acid (QXC) or 3-hydroxyquinaldic acid (HQA);…”

Section: 214mentioning

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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Nonproteinogenic Amino Acid Building Blocks for Nonribosomal Peptide and Hybrid Polyketide Scaffolds

Cited by 354 publications

References 241 publications

Antifungal activity of Brevibacillus laterosporus JX-5 and characterization of its antifungal components

Antifungal activity of Brevibacillus laterosporus JX-5 and characterization of its antifungal components

Genome mining unearths a hybrid nonribosomal peptide synthetase-like-pteridine synthase biosynthetic gene cluster

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

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