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.
Biosynthesis of mycophenolic acid / L. Canonica, W. Kroszczynski, B.M. Ranzi, B. Rindone, E. Santaniello, C. Scolastico. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - :0(1972), pp. 2639-2643.
|Titolo:||Biosynthesis of mycophenolic acid|
SANTANIELLO, ENZO (Penultimo)
SCOLASTICO, CARLO (Ultimo)
|Settore Scientifico Disciplinare:||Settore BIO/10 - Biochimica|
|Data di pubblicazione:||1972|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1039/P19720002639|
|Appare nelle tipologie:||01 - Articolo su periodico|