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Stereochemistry of cercosporin |
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| Authors: | Gianluca Nasini Lucio Merlini Giovanni Dario Andreetti Gabriele Bocelli Paolo Sgarabotto |
| Institution: | Centro del C.N.R. per le Sostanze Organiche Naturali, Dipartimento di Chimica, Politecnico di Milano, 20133 Milano, Italy;Istituto di Biochimica Generale, Università di Milano, Via Celoria, 2 - 20133 Milano, Italy;Istituto di Strutturistica Chimica, Università di Parma, Centro di Studio per la Strutturistica Diffrattometrica del C.N.R., Via D''Azeglio, 85 - 43100 Parma, Italy |
| Abstract: | The absolute configuration of the asymmetric carbons and the axial chirality of the natural mold metabolite cercosporin (from .) have been established on the basis of X-ray analysis and chemical reactions. The results confirm the inherent dissymmetry of the perylenequinone ring, the twisting of which gives rise to the diastereoisomer isocercosporin. The energy barrier for the conversion of cercosporin into isocercosporin has been evaluated. |
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