The S2 Oxygen Atoms Are Essential for the Pronounced Fungitoxicity of the Sulfur-Rich Natural Product, Dysoxysulfone
Sharon A. Bewick A , Stephen Duffy A , Stephen P. Fletcher A , Richard F. Langler A C , Heather G. Morrison A , Erin M. O’Brien A , Charles Ross B D and Vanessa C. Stephenson AA Department of Chemistry, Mount Allison University, Sackville, New Brunswick E4L 1G8, Canada.
B Department of Structural Biology, St. Jude Children's Research Hospital, Memphis, TN 38105, USA.
C Corresponding author (organic chemistry). Email: rlangler@mta.ca
D Corresponding author (crystallography). Email: charles.ross@stjude.org
Australian Journal of Chemistry 58(3) 218-223 https://doi.org/10.1071/CH03253
Submitted: 22 April 2003 Accepted: 16 June 2004 Published: 15 March 2005
Abstract
Synthesis and antifungal testing of 2,4,5,7,9-pentathiadecane 9,9-dioxide has established that the absence of oxygen atoms on S2 significantly attenuates fungitoxicity in accord with our earlier proposal. Attempts to convert that compound into dysoxysulfone led to the discovery of a novel oxidative conversion of unsymmetrical γ-sulfonyl disulfides into the corresponding symmetrical γ-sulfonyl disulfides.
Acknowledgments
The authors acknowledge technical assistance from M. Marchand and D. Ryan. The 13C and 270 MHz 1H NMR spectra were obtained by D. Durant, and the mass spectra by R. Smith.
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