Due to recent advance in theoretical predictions of chiroptical properties, and the progress in computation and instrumental technology, all three methods of Optical Rotatory Dispersion (ORD), Electronic (ECD) and Vibrational Circular Dichroism (VCD) can provide nowadays very reliable approaches for assignment of the molecular absolute configuration (AC) in solution. However, in some instances, to avoid any ambiguity in configurational assignment, the use of more than one single method is justified. In this work we present a determination of AC of two bioactive fungal metabolites, phyllostin[1] and scytolide,[2] by combined employment of theoretical/experimental analysis of their ORD, ECD, and VCD properties. We provide evidences justifying the necessity of multiple methods for safest possible AC assignment of both compounds. References [1] A. Evidente, A. Cimmino, A. Andolfi, M. Vurro, M.C. Zonno, A. Motta, J. Agric. Food Chem. 56 884 (2008) [2] W.A. Ayer, Y. Fukazawa, H. Orszanska, Nat. Prod. Lett. 2 77 (1993)
Absolute configuration of fungal metabolites phyllostin and scytolide by ORD, ECD, and VCD computational analysis / G., Mazzeo; Andolfi, Anna; Cimmino, Alessio; A. G., Petrovic; S., Superchi; Evidente, Antonio; N. B. e. r. o. v., A.. - (2012). (Intervento presentato al convegno Vibrational Optical Activity: Interplay of Theory and Experiment tenutosi a Pisa, Italy).
Absolute configuration of fungal metabolites phyllostin and scytolide by ORD, ECD, and VCD computational analysis.
ANDOLFI, ANNA;CIMMINO, ALESSIO;EVIDENTE, ANTONIO;
2012
Abstract
Due to recent advance in theoretical predictions of chiroptical properties, and the progress in computation and instrumental technology, all three methods of Optical Rotatory Dispersion (ORD), Electronic (ECD) and Vibrational Circular Dichroism (VCD) can provide nowadays very reliable approaches for assignment of the molecular absolute configuration (AC) in solution. However, in some instances, to avoid any ambiguity in configurational assignment, the use of more than one single method is justified. In this work we present a determination of AC of two bioactive fungal metabolites, phyllostin[1] and scytolide,[2] by combined employment of theoretical/experimental analysis of their ORD, ECD, and VCD properties. We provide evidences justifying the necessity of multiple methods for safest possible AC assignment of both compounds. References [1] A. Evidente, A. Cimmino, A. Andolfi, M. Vurro, M.C. Zonno, A. Motta, J. Agric. Food Chem. 56 884 (2008) [2] W.A. Ayer, Y. Fukazawa, H. Orszanska, Nat. Prod. Lett. 2 77 (1993)I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
