Resolution and Absolute Configuration Assignment of a Natural Racemic Chromane from Peperomia obtusifolia (Piperaceae)
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Data
2009-10-01
Autores
Batista, Joao Marcos [UNESP]
Lopez, Silvia Noeli [UNESP]
Mota, Jonas da Silva
Vanzolini, Kenia Lourenco
Cass, Quezia Bezerra
Rinaldo, Daniel
Vilegas, Wagner [UNESP]
Bolzani, Vanderlan da Silva [UNESP]
Kato, Massuo Jorge
Furlan, Maysa [UNESP]
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Wiley-liss
Resumo
The resolution of the natural racemic chromane 3,4-dihydro-5-hydroxy-2,7-dimethyl-8-(3 ''-methyl-2 ''-butenyl)-2-(4'-methyl-1',3'-pentadienyl)-2H-1-benzopyran-6-carboxylic acid (1) isolated from the leaves of Peperomia obtusifolia has been accomplished using stereoselective HPLC. The absolute coil figuration of the resolved enantiomers was determined by the analysis of optical rotations and CD spectra. The finding of a racemic mixture instead of an enantiomerically pure metabolite raises questions about the final steps in the biosynthesis of this class of natural products, suggesting that the intramolecular chromane ring formation step may not be enzymatically controlled at all in P. obtusifolia. Chirality 21:799-801, 2009. (C) 2008 Wiley-Liss, Inc.
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natural products, enantioseparation, circular dichroism, optical rotation, absolute configuration
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Chirality. Hoboken: Wiley-liss, v. 21, n. 9, p. 799-801, 2009.