Biosynthesis of mycophenolic acid
| Autor: | Luigi Canonica, W. Kroszczynski, E. Santaniello, Carlo Scolastico, Bruno Rindone, Bianca M. Ranzi |
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| Rok vydání: | 1972 |
| Předmět: | |
| Zdroj: | Journal of the Chemical Society, Perkin Transactions 1. :2639 |
| ISSN: | 1364-5463 0300-922X |
| DOI: | 10.1039/p19720002639 |
| Popis: | Incorporation experiments with labelled potential biosynthetic intermediates suggest that the methyl group at C-4 of the phthalide system in mycophenolic acid is introduced at the tetraketide stage. This then gives way to the aromatic system, which is further oxidised to 5,7-dihydroxy-4-methylphthalide. The isolation of 6-farnesyl-5,7-di-hydroxy-4-methylphthalide from the culture and the high incorporation of this compound into mycophenolic acid indicate that the most important process for the biosynthesis of the side-chain is the introduction of a C15 terpene chain followed by oxidative fission at the appropriate double bond. ‘Enzymic trap’ experiments confirm these results. Alternative pathways for the biosynthesis of the side-chain through 6-geranyl-5.7-dihydroxy-4-methyl-phthalide are discussed. |
| Databáze: | OpenAIRE |
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