Issue 77, 2015
From the journal:

Chemical Communications

Biomimetic synthesis of Tramadol†

Florine Lecerf-Schmidt,‡ab   Romain Haudecoeur,‡ab   Basile Peres,ab   Marcos Marçal Ferreira Queiroz,c   Laurence Marcourt,c   Soura Challal,c   Emerson Ferreira Queiroz,c   Germain Sotoing Taiwe,d   Thierry Lomberget,e   Marc Le Borgne,e   Jean-Luc Wolfender,c   Michel De Waard,f   Richard J. Robinsg  and  Ahcène Boumendjel*ab  

* Corresponding authors

a Univ. Grenoble-Alpes, DPM UMR 5063, F-38041 Grenoble, France
E-mail: Ahcene.Boumendjel@ujf-grenoble.fr

b CNRS, DPM UMR 5063, F-38041 Grenoble, France

c School of Pharmaceutical Sciences, EPGL, University of Geneva, University of Lausanne, quai Ernest-Ansermet 30, CH-1211 Geneva 4, Switzerland

d Department of Zoology and Animal Physiology, Faculty of Science, University of Buea, P.O. Box 63, Buea, Cameroon

e Université de Lyon, Université de Lyon 1, Faculté de Pharmacie – ISPB, EA 4446 B2C, 69373 Lyon, France

f Unité Inserm U836, Grenoble Institute of Neuroscience, Site Santé, 38700 La Tronche, France

g Elucidation of Biosynthesis by Isotopic Spectrometry Group, CEISAM Laboratory, University of Nantes – CNRS UMR 6230, 44322 Nantes, France

Abstract

Tramadol has recently been isolated from the roots and bark of Nauclea latifolia. A plausible biosynthetic pathway has been proposed and the product–precursor relationship has been probed by 13C position-specific isotope analysis. By further exploring this pathway, we demonstrate that a key step of the proposed pathway can be achieved using mild conditions that mimic in vivo catalysis.

Graphical abstract: Biomimetic synthesis of Tramadol

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Article information

DOI
https://doi.org/10.1039/C5CC05948H
Article type
Communication
Submitted
17 Jul 2015
Accepted
05 Aug 2015
First published
05 Aug 2015

Chem. Commun., 2015,51, 14451-14453

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Biomimetic synthesis of Tramadol

F. Lecerf-Schmidt, R. Haudecoeur, B. Peres, M. M. Ferreira Queiroz, L. Marcourt, S. Challal, E. Ferreira Queiroz, G. Sotoing Taiwe, T. Lomberget, M. Le Borgne, J. Wolfender, M. De Waard, R. J. Robins and A. Boumendjel, Chem. Commun., 2015, 51, 14451 DOI: 10.1039/C5CC05948H

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