The conversion of cyclopenin into viridicatin

White, James D.; Dimsdale, M. J.

doi:10.1039/c2969001285b

Cited by 22 publications

(13 citation statements)

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“…Because the spontaneous transformation of 10 to 3 proceeded quickly in an aqueous buffer at 30 °C, the conversion is likely nonenzymatic. Thus, we proposed a mechanism of formation of 3 from 10 that was similar to the previously proposed mechanism of formation of 4 . Epoxide opening initiated by donation of the methoxy oxygen lone pair followed by elimination of carbon dioxide and methylamine in the form of methyl isocyanate can lead to the transformation of the 6,7‐bicyclic system of 10 into the 6,6‐bicyclic quinolone of 3 …”

Section: Detailed Biosynthetic Pathways Of Natural Productssupporting

confidence: 69%

Elucidation of Biosynthetic Pathways of Natural Products

Kishimoto

Tsunematsu

Sato

et al. 2017

The Chemical Record

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During the last decade, we have revealed biosynthetic pathways responsible for the formation of important and chemically complex natural products isolated from various organisms through genetic manipulation. Detailed in vivo and in vitro characterizations enabled elucidation of unexpected mechanisms of secondary metabolite biosynthesis. This personal account focuses on our recent efforts in identifying the genes responsible for the biosynthesis of spirotryprostatin, aspoquinolone, Sch 210972, pyranonigrin, fumagillin and pseurotin. We exploit heterologous reconstitution of biosynthetic pathways of interest in our study. In particular, extensive involvement of oxidation reactions is discussed. Heterologous hosts employed here are Saccharomyces cerevisiae, Aspergillus nidulans and A. niger that can also be used to prepare biosynthetic intermediates and product analogs by engineering the biosynthetic pathways using the knowledge obtained by detailed characterizations of the enzymes. (998 char.).

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Section: Detailed Biosynthetic Pathways Of Natural Productssupporting

confidence: 69%

Elucidation of Biosynthetic Pathways of Natural Products

Kishimoto

Tsunematsu

Sato

et al. 2017

The Chemical Record

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“…47–48 At this stage an enzyme known as cyclopenase 50–51 converts the epoxy-6,7-bicyclic framework to the 6,6-bicyclic quinolone viridicatol (figure 7c). Viridicatol formation is attended by production of CO 2 and methyl amine (thought to arise from methyl isocyanate, which forms as coproduct when this conversion is carried out non-enzymatically 52–53 ). Viridicatol is processed further in Penicillium species by tandem O -methylation of the two –OH groups, introduction of two additional –OH groups (perhaps by hydratase and hydroxylase action, respectively), followed by prenyl transferase action to yield peniprequinolones.…”

Section: Pathways Utilizing Tethered Ant-x Dipeptidyl Intermediatesmentioning

confidence: 99%

Short Pathways to Complexity Generation: Fungal Peptidyl Alkaloid Multicyclic Scaffolds from Anthranilate Building Blocks

et al. 2013

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Complexity generation in naturally occurring peptide scaffolds can occur either by posttranslational modifications of nascent ribosomal proteins or through post assembly line tailoring of nonribosomal peptides. Short enzymatic pathways utilizing bimodular and trimodular nonribosomal peptide synthetase (NRPS) assembly lines, followed by tailoring oxygenases and/or prenyltransferases, efficiently construct complex fungal peptidyl alkaloid scaffolds in Aspergilli, Neosartorya, and Penicillium species. Use of the nonproteinogenic amino acid anthranilate as chain-initiating building block and chain-terminating intramolecular nucleophile leads efficiently to peptidyl alkaloid scaffolds with two to seven fused rings.

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“…In operations research the best-known approaches to modelling and solving such multi-stage models are "Dynamic Programming" and "Branch-and-Bound" methods [Beckmann 1968;Bellman 1957;Gillett 1976;Nemhauser 1966;Norman 1975;White 1969]. We shall first sketch the basic crisp approach before we discuss fuzzy versions.…”

Section: Introductionmentioning

confidence: 99%