Structures and biosynthesis of 12-membered macrocyclic depsipeptides from Streptomyces sp. ML55

Li, Xiang; Zvanych, Rostyslav; Torchia, Jonathon; Magarvey, Nathan A.

doi:10.1016/j.bmcl.2013.05.042

Cited by 7 publications

(10 citation statements)

References 4 publications

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“…Streptomyces sp. ML55 in a medium consisting of glycerin, molasses, casein, polypeptone led to the isolation of three novel antimycins, JBIR-02 ( 71 ), JBIR-06 ( 72 ), and JBIR-52 ( 73 ), while this strain had capacity to produce two novel depsipeptides ( 74–75 ) in GYM medium (Ueda et al, 2007, 2008; Kozone et al, 2009; Li X. et al, 2013). An ant-derived actinomycete Streptomyces sp.…”

Section: Variation Of Mediummentioning

confidence: 99%

Exploring Structural Diversity of Microbe Secondary Metabolites Using OSMAC Strategy: A Literature Review

et al. 2019

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Microbial secondary metabolites (MSMs) have played and continue to play a highly significant role in the drug discovery and development process. Genetically, MSM chemical structures are biologically synthesized by microbial gene clusters. Recently, however, the speed of new bioactive MSM discovery has been slowing down due to consistent employment of conventional cultivation and isolation procedure. In order to alleviate this challenge, a number of new approaches have been developed. The strategy of one strain many compounds (OSMAC) has been shown as a simple and powerful tool that can activate many silent biogenetic gene clusters in microorganisms to make more natural products. This review highlights important and successful examples using OSMAC approaches, which covers changing medium composition and cultivation status, co-cultivation with other strain(s), adding enzyme inhibitor(s) and MSM biosynthetic precursor(s). Available evidences had shown that variation of cultivation condition is the most effective way to produce more MSMs and facilitate the discovery of new therapeutic agents.

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Section: Variation Of Mediummentioning

confidence: 99%

Exploring Structural Diversity of Microbe Secondary Metabolites Using OSMAC Strategy: A Literature Review

et al. 2019

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“…13,60 Evidence for this pathway has been provided by gene disruption experiments, heterologous expression of the gene cluster, and biochemical analysis. 59 Similarly, AntB has been shown to generate diversity at the C8 acyloxy group, and Streptomyces DantB mutants have been used to produce several deacylated antimycins (40,42,43,45,69,70). 52,57 Moreover, the activities of AntB, C, D, and E were individually characterized in vitro, and the enzymatic synthesis of the dilactone scaffold of antimycin was achieved with puried AntC, D, E, F, G, and M and their corresponding substrates and cofactors.…”

Section: Biosynthesismentioning

confidence: 99%

“…ML55 (soil, Taketomi Island, Okinawa Prefecture, Japan) during screening for down-regulators of GRP-78 (Fig. 40 7,39 Tandem mass spectrometry analysis further revealed that this strain produced two additional analogues (51, 52) with either a 3-aminosalicylic acid or a 2,3-hydroxybenzoic acid in place of the usual 3-formamidosalicylate unit.…”

Section: Introductionmentioning

confidence: 99%

Antimycin-type depsipeptides: discovery, biosynthesis, chemical synthesis, and bioactivities

et al. 2016

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Covering: up to 2016Antimycin-type depsipeptides are a family of natural products with great structural diversity and outstanding biological activities. These compounds have typically been isolated from actinomycetes and are generated from hybrid nonribosomal peptide synthetase (NRPS)-polyketide synthase (PKS) assembly lines. This review covers the literature on the four classes of antimycin-type depsipeptides, which differ by macrolactone ring size, and it discusses the discovery, biosynthesis, chemical synthesis, and biological activities of this family of compounds.

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“…228,229 They all have at least one C-A-KR-T depsipeptide module for incorporation of keto acids into depsipeptides in elongation but can have multiple extras which increase the lactone ring size. [232][233][234] Awakawa and coworkers were able to generate novel antimycin-like compounds by employing a shuffling and deletions strategy between the JBIR-06 and neoantimycin NRPSs. 235 This led to functional chimeric depsipeptide synthetases, an elegant proof of concept of the bioengineering potential of these megaenzymes.…”

Section: Depsipeptides With Ester Bonds Formed During Both Elongatimentioning

confidence: 99%

“…Antimycin‐like peptides are synthesized by mixed PKS‐NRPS systems 228,229 . They all have at least one C‐A‐KR‐T depsipeptide module for incorporation of keto acids into depsipeptides in elongation but can have multiple extras which increase the lactone ring size 232–234 . Awakawa and coworkers were able to generate novel antimycin‐like compounds by employing a shuffling and deletions strategy between the JBIR‐06 and neoantimycin NRPSs 235 .…”

Section: Depsipeptides With Ester Bonds Formed During Both Elongationmentioning

confidence: 99%

Biosynthesis of depsipeptides, or Depsi: The peptides with varied generations

Alonzo

Schmeing

2020

Protein Science

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Depsipeptides are compounds that contain both ester bonds and amide bonds. Important natural product depsipeptides include the piscicide antimycin, the K + ionophores cereulide and valinomycin, the anticancer agent cryptophycin, and the antimicrobial kutzneride. Furthermore, database searches return hundreds of uncharacterized systems likely to produce novel depsipeptides. These compounds are made by specialized nonribosomal peptide synthetases (NRPSs). NRPSs are biosynthetic megaenzymes that use a module architecture and multi-step catalytic cycle to assemble monomer substrates into peptides, or in the case of specialized depsipeptide synthetases, depsipeptides. Two NRPS domains, the condensation domain and the thioesterase domain, catalyze ester bond formation, and ester bonds are introduced into depsipeptides in several different ways. The two most common occur during cyclization, in a reaction between a hydroxy-containing side chain and the C-terminal amino acid residue in a peptide intermediate, and during incorporation into the growing peptide chain of an α-hydroxy acyl moiety, recruited either by direct selection of an α-hydroxy acid substrate or by selection of an α-keto acid substrate that is reduced in situ. In this article, we discuss how and when these esters are introduced during depsipeptide synthesis, survey notable depsipeptide synthetases, and review insight into bacterial depsipeptide synthetases recently gained from structural studies.

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Structures and biosynthesis of 12-membered macrocyclic depsipeptides from Streptomyces sp. ML55

Cited by 7 publications

References 4 publications

Exploring Structural Diversity of Microbe Secondary Metabolites Using OSMAC Strategy: A Literature Review

Exploring Structural Diversity of Microbe Secondary Metabolites Using OSMAC Strategy: A Literature Review

Antimycin-type depsipeptides: discovery, biosynthesis, chemical synthesis, and bioactivities

Biosynthesis of depsipeptides, or Depsi: The peptides with varied generations

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