Issue 5, 2012
From the journal:

Chemical Science

Stephanie N. Dupuis,a   Andrew W. Robertson,a   Thomas Veinot,b   Susan M. A. Monro,c   Susan E. Douglas,d   Ray T. Syvitski,ad   Kerry B. Goralski,be   Sherri A. McFarlandc  and  David L. Jakeman*ab  

* Corresponding authors

a Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada

b College of Pharmacy, Dalhousie University, 5968 College St., PO Box 15,000, Halifax, Nova Scotia, Canada
E-mail: david.jakeman@dal.ca

c Department of Chemistry, Acadia University, Wolfville, Nova Scotia, Canada

d Institute for Marine Biosciences, National Research Council of Canada, Halifax, Nova Scotia, Canada

e Department of Pharmacology, Dalhousie University, Halifax, Nova Scotia, Canada

Abstract

Growth of Streptomyces venezuelae ISP5230 with O-propargyl-L-serine led to the efficient production of an alkyne-containing jadomycin. The installed alkyne functionality provided a uniquely reactive handle within the natural product and was subsequently reacted with a series of azides to afford an eight-member library of jadomycin triazoles. The compounds were evaluated for their DNA cleavage, antibacterial and cytotoxic properties.

Graphical abstract: Synthetic diversification of natural products: semi-synthesis and evaluation of triazole jadomycins

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Article information

DOI
https://doi.org/10.1039/C2SC00663D
Article type
Edge Article
Submitted
12 Sep 2011
Accepted
30 Jan 2012
First published
31 Jan 2012

Chem. Sci., 2012,3, 1640-1644

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Synthetic diversification of natural products: semi-synthesis and evaluation of triazole jadomycins

S. N. Dupuis, A. W. Robertson, T. Veinot, S. M. A. Monro, S. E. Douglas, R. T. Syvitski, K. B. Goralski, S. A. McFarland and D. L. Jakeman, Chem. Sci., 2012, 3, 1640 DOI: 10.1039/C2SC00663D

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