59896-20-7Relevant academic research and scientific papers
A convenient laboratory procedure for the preparation of cortalcerone, a fungal antibiotic β-pyrone
Gabriel,Volc,Kubatova,Palkova,Pospisek
, p. 297 - 301 (1994)
The unsaturated β-pyrone antibiotic cotalcerone (2-hydroxy-6H-3-pyrone-2-carboxaldehyde hydrate, was prepared from aqueous macerates of mycelia from the basidiomycete Corticium caeruleum, by selective solubilization and precipitation followed by repeated silica-gel column chromatography.Subsequent studies showed that cortalcerone is derived from D-glucose through a multi-step pathway involving oxidation of D-glucose.
Synthesis of the antibiotic cortalcerone from D-glucose using pyranose 2-oxidase and a novel fungal enzyme, aldos-2-ulose dehydratase
Koths, Kirston,Halenbeck, Robert,Moreland, Margaret
, p. 59 - 76 (1992)
Using two enzymes purified from the white-rot fungus, Polyporus obtusus, 5percent solutions of D-glucose have been quantitatively converted in vitro into D-arabino-hex-2-ulose (D-glucosone) and subsequently into a compound having antimicrobial activity.The antibiotic has been shown by nuclear magnetic resonance and mass spectroscopy to be chemically identical to a previously described fungal metabolite known as cortalcerone.Based on kinetic analysis o the synthetic process, a pathway for the biosynthesis of cortalcerone is proposed, involving both chemical rearrangement and enzymatically catalyzed steps.Two enzymes, pyranose 2-oxidase and a previously uncharacterized D-arabino-hexos-2-ulose-utilizing enzyme, may be sufficient for the biosynthesis of cortalcerone from glucose in vivo.The D-arabino-hexos-2-ulose-utilizing enzyme dehydrates certain aldosuloses and has been named aldos-2-ulose dehydratase.The enzyme, which appears to be a dimer of 95-kDa subunits, has been purified 450-fold.Additional properties of aldos-2-ulose dehydratase are described, including its apparent ability to catalyze two different steps in the proposed biosynthetic pathway for cortalcerone.
