1,5-Anhydro-D-fructose is a breakdown product of starch and glycogen catabolism in bacteria and fungi. Its metabolism in bacteria is shown in the Starch Oligomer Pathway. In white rot fungus and morels, the bifunctional enzyme aldos-2-ulose dehydratase catalyzes the transformation of 1,5-anhydro-D-fructose to ascopyrone M and then to microthecin (Yu et al., 2004). In Peziza echinospora, the 1,5-anhydro-D-fructose intermediate is converted to ascopyrone M and then to 5-epipentenomycin. Ascopyrone M, ascopyrone P, and ascopyrone T are keto-enol tautomers. Ascopyrone T can be nonenzymatically dihydrated to ascopyrone T1 or enzymatically reduced to 2(S)-dihydroascopyrone T (Deffieux G, Vercauteren J, Baute M-A, Neveu A, Baute R, Phytochemistry, 36: 849-852, 1994).
The following is a text-format 1,5-anhydro-D-fructose (fungal) pathway map. Organisms that can initiate the pathway are given, but other organisms may also carry out later steps. Follow the links for more information on compounds or reactions. This map is also available in graphic (12k) format.
1,5-Anhydro-D-fructose <----------- from the Starch Oligomer pathway Aspergillus niger Morchella costata Morchella vulgaris Peziza ostracoderma Anthracobia melaloma | | 1,5-anhydro-D- | fructose dehydratase | or | aldos-2-ulose | dehydratase | | aldos-2-ulose v dehydratase Ascopyrone M -------------------> Microthecin | | | | 1,5-anhydro-D- ascopyrone P | | fructose dehydratase tautomerase | +---------------------> 5-Epipentenomycin I | | v Ascopyrone P | | A | (spontaneous) | | v B (abiotic) Ascopyrone T -------------------> Ascopyrone T1 | | ascopyrone T | reductase | | | v 2(S)-Dihydro- ascopyrone T
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