Issue 21, 2012
From the journal:

Organic & Biomolecular Chemistry

VCD to determine absolute configuration of natural product molecules: secolignans from Peperomia blanda†

Lidiane G. Felippe,‡a   João M. Batista Jr.,‡*a   Debora C. Baldoqui,b   Isabele R. Nascimento,a   Massuo J. Kato,c   Yanan He,d   Laurence A. Nafiede  and  Maysa Furlan*a  

* Corresponding authors

a Organic Chemistry Department, Institute of Chemistry, São Paulo State University – UNESP, Araraquara, SP 14800-900, Brazil
E-mail: maysaf@reitoria.unesp.br, joaombj@hotmail.com
Fax: +55-16-3301-9692
Tel: +55-16-3301-9661

b Department of Chemistry, Maringá State University, Maringá, PR, Brazil

c Department of Fundamental Chemistry, Institute of Chemistry, University of São Paulo, SP 05508-000, Brazil

d BioTools, Inc. Jupiter, FL 33458, USA

e Department of Chemistry, Syracuse University, Syracuse, NY 13244-4100, USA

Abstract

The absolute configuration and solution-state conformers of three peperomin-type secolignans isolated from Peperomia blanda (Piperaceae) are unambiguously determined by using vibrational circular dichroism (VCD) spectroscopy associated with density functional theory (DFT) calculations. Advantages of VCD over the electronic form of CD for the analysis of diastereomers are also discussed. This work extends our growing knowledge about secondary metabolites within the Piperaceae family species while providing a definitive and straightforward method to assess the absolute stereochemistry of secolignans.

Graphical abstract: VCD to determine absolute configuration of natural product molecules: secolignans from Peperomia blanda

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Article information

DOI
https://doi.org/10.1039/C2OB25109D
Article type
Paper
Submitted
14 Jan 2012
Accepted
03 Apr 2012
First published
04 Apr 2012

Org. Biomol. Chem., 2012,10, 4208-4214

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VCD to determine absolute configuration of natural product molecules: secolignans from Peperomia blanda

L. G. Felippe, J. M. Batista Jr., D. C. Baldoqui, I. R. Nascimento, M. J. Kato, Y. He, L. A. Nafie and M. Furlan, Org. Biomol. Chem., 2012, 10, 4208 DOI: 10.1039/C2OB25109D

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