Determination of the structure of fusaproliferin by1H-NMR and distance geometry |
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Authors: | Dr Cesare Manetti Vincenzo Fogliano Alberto Ritieni Antonello Santini Giacomino Randazzo Antonio Logrieco Luisa Mannina Anna Laura Segre |
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Institution: | (1) Dipartimento di Scienza degli Alimenti dell'Università degli Studi di Napoli Federico II, Portici, Napoli, Italy;(2) Istituto di Tossine e Micotossine del CNR, Bari, Italy;(3) Area della Ricerca di Roma, Montelibretti, Roma, Italy;(4) Istituto di Strutturistica Chimica C.N.R., Roma, Italy;(5) Dipartimento di Chimica, Università La Sapienza , Piazzale Aldo Moro, 5-00185 Roma, Italy |
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Abstract: | The absolute configuration of fusaproliferin, a toxic metabolite produced byFusarium proliferation, was determined by the combined use of1H NMR and distance geometry. The configuration of double bonds has been determined in agreement with NOESY buildup data. An R configuration for C10 was determined using Mosher's method. Processing the constraints obtained from NOESY experiments with a distance geometry program, a limited number (80) of possible structures was derived. An agglomerative nonhierarchical method of clustering was used in order to place these structures into classes suggested by the data, and not previously defined in any way. This statistical method showed that indeed the structures could be grouped in four classes. One of these classes is represented by a single structure, with the highest sum of violations and was discarded. All other structures have the same chirality; respectively S for C14 and R for C15. In solution the overall conformation is quite well defined in the region of the five-member ring and the planes of double bonds C2–C3 and C11–C12, while near to C8 and C9 internal flexibility appears evident. |
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Keywords: | NMR distance geometry cluster analysis absolute configuration fusaproliferin |
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