The nonadrides. Part V. Biosynthesis of glauconic acid

Bloomer, J. L.; Moppett, C. E.; Sutherland, J. K.

doi:10.1039/j39680000588

Cited by 22 publications

(20 citation statements)

References 1 publication

(1 reference statement)

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“…Sutherland and coworkers reported the results of [1- C 2 ]-succinate which suggested that oxaloacetate was a more likely precursor than pyruvate. 55 The results supported a previous suggestion that a polyketide or fatty acid is condensed with oxaloacetate to make a citrate-like intermediate which dehydrates to the observed maleic anhydride 48 (Scheme 4). 46 The symmetrical incorporation of the labels strongly supported the idea that dimerisation of such an intermediate formed the nine-membered ring in 39 etc.…”

Section: The Maleidridessupporting

confidence: 80%

“…This observation supported the proposed mechanism of formation of the nonadrides as either a concerted 6p + 4p cyclodimerisation, or a stepwise polar process (Scheme 4A). 55 Baldwin and coworkers extensively reinvestigated this biomimetic process using an n-pentenyl maleic anhydride 50 (rather than the n-butenyl analogue 48 used by Sutherland) during the late 1990s. Although still low, optimisation of reaction conditions resulted in yield improvements (up to 8.5% for 51), and the isolation of isomeric compounds with six-(53) and seven-membered rings (52) in similar amounts.…”

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confidence: 99%

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Classic fungal natural products in the genomic age: the molecular legacy of Harold Raistrick

Schor

Cox

2018

Nat. Prod. Rep.

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Harold Raistrick was involved in the discovery of many of the most important classes of fungal metabolites during the 20th century. This review focusses on how these discoveries led to developments in isotopic labelling, biomimetic chemistry and the discovery, analysis and exploitation of biosynthetic gene clusters for major classes of fungal metabolites including: alternariol; geodin and metabolites of the emodin pathway; maleidrides; citrinin and the azaphilones; dehydrocurvularin; mycophenolic acid; and the tropolones. Key recent advances in the molecular understanding of these important pathways, including the discovery of biosynthetic gene clusters, the investigation of the molecular and chemical aspects of key biosynthetic steps, and the reengineering of key components of the pathways are reviewed and compared. Finally, discussion of key relationships between metabolites and pathways and the most important recent advances and opportunities for future research directions are given.

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Section: The Maleidridessupporting

confidence: 80%

mentioning

confidence: 99%

Classic fungal natural products in the genomic age: the molecular legacy of Harold Raistrick

Schor

Cox

2018

Nat. Prod. Rep.

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“…Another red pigment, glauconic acid, is probably the oldest product mentioned in this review. In fact, this nonadride compound has been known since 1931 [ 59 ], mainly from studies concerning its biosynthetic pathway, which indicate that it derives through several steps involving substitutions in citric acid and dimerization of a C 9 anhydride unit [ 60 ], or from succinate [ 61 ]. However, no detailed investigation of its bioactivity seems to have been accomplished so far.…”

Section: Structures and Properties Of Secondary Metabolites From Mmentioning

confidence: 99%

Secondary Metabolites of Mangrove-Associated Strains of Talaromyces

2018

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Boosted by the general aim of exploiting the biotechnological potential of the microbial component of biodiversity, research on the secondary metabolite production of endophytic fungi has remarkably increased in the past few decades. Novel compounds and bioactivities have resulted from this work, which has stimulated a more thorough consideration of various natural ecosystems as conducive contexts for the discovery of new drugs. Thriving at the frontier between land and sea, mangrove forests represent one of the most valuable areas in this respect. The present paper offers a review of the research on the characterization and biological activities of secondary metabolites from manglicolous strains of species belonging to the genus Talaromyces. Aspects concerning the opportunity for a more reliable identification of this biological material in the light of recent taxonomic revisions are also discussed.

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“…Barton und Sutherland postulierten darüber hinaus, dass das Monomer 9 ein modifiziertes Produkt des Citratzyklus ist, das aus einem polyketidischen Hexanoat und Oxalactetat entsteht . Gestützt wurde diese Hypothese durch Fütterungsstudien mit Isotopen‐markierten Substraten . Darauf basierend sollte ein mögliches Maleidrid‐Biosynthesecluster (Maleidrid‐BGC) zusätzlich zum Gen einer vollständig reduzierenden Polyketidsynthase (hrPKS) auch ein Gen enthalten, das für ein Citratsynthase‐ähnliches Enzym codiert …”

Section: Figureunclassified