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Resolution and Absolute Configuration Assignment of a Natural Racemic Chromane from Peperomia obtusifolia (Piperaceae)

Authors
  • 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
Publication Date
Jan 01, 2009
Source
Biblioteca Digital da Produção Intelectual da Universidade de São Paulo (BDPI/USP)
Keywords
Language
English
License
Unknown
External links

Abstract

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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