Issue 4, 2006
From the journal:

Organic & Biomolecular Chemistry

Spontaneity in the patellamide biosynthetic pathway

Bruce F. Milne,a   Paul F. Long,b   Antonio Starcevic,c   Daslav Hranuelic  and  Marcel Jaspars*d  

* Corresponding authors

a Centro de Estudos de Química Orgânica, Fitoquímica e Farmacologia, Faculdade de Farmácia, Universidade do Porto, Rua Aníbal Cunha 164, Porto, Portugal

b School of Pharmacy, University of London, 29/39 Brunswick Square, London, UK

c Faculty of Food Technology and Biotechnology, University of Zagreb, Pierottijeva 6, Zagreb, Croatia

d Marine Natural Products Laboratory, Department of Chemistry, University of Aberdeen, Old Aberdeen, Scotland, UK
E-mail: m.jaspars@abdn.ac.uk
Fax: +44 1224 272 921

Abstract

Post-translationally modified ribosomal peptides are unusual natural products and many have potent biological activity. The biosynthetic processes involved in their formation have been delineated for some, but the patellamides represent a unique group of these metabolites with a combination of a macrocycle, small heterocycles and D-stereocentres. The genes encoding for the patellamides show very low homology to known biosynthetic genes and there appear to be no explicit genes for the macrocyclisation and epimerisation steps. Using a combination of literature data and large-scale molecular dynamics calculations with explicit solvent, we propose that the macrocyclisation and epimerisation steps are spontaneous and interdependent and a feature of the structure of the linear peptide. Our study suggests the steps in the biosynthetic route are heterocyclisation, macrocyclisation, followed by epimerisation and finally dehydrogenation. This study is presented as testable hypothesis based on literature and theoretical data to be verified by future detailed experimental investigations.

Graphical abstract: Spontaneity in the patellamide biosynthetic pathway

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Article information

DOI
https://doi.org/10.1039/B515938E
Article type
Paper
Submitted
09 Nov 2005
Accepted
09 Dec 2005
First published
09 Jan 2006

Org. Biomol. Chem., 2006,4, 631-638

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Spontaneity in the patellamide biosynthetic pathway

B. F. Milne, P. F. Long, A. Starcevic, D. Hranueli and M. Jaspars, Org. Biomol. Chem., 2006, 4, 631 DOI: 10.1039/B515938E

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