Artículos de revistas
Resolution and Absolute Configuration Assignment of a Natural Racemic Chromane from Peperomia obtusifolia (Piperaceae)
Fecha
2009Registro en:
CHIRALITY, v.21, n.9, p.799-801, 2009
0899-0042
10.1002/chir.20676
Autor
BATISTA JR., Joao Marcos
LOPEZ, Silvia Noeli
MOTA, Jonas da Silva
VANZOLINI, Kenia Lourenco
CASS, Quezia Bezerra
RINALDO, Daniel
VILEGAS, Wagner
BOLZANI, Vanderlan da Silva
KATO, Massuo Jorge
FURLAN, Maysa
Institución
Resumen
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.