Determination of the Complete Absolute Configuration of Petriellin A
Luigi Aurelio A B , Robert T. C. Brownlee A , Jason Dang A C , Andrew B. Hughes A E and Gideon M. Polya DA Department of Chemistry, La Trobe University, Bundoora VIC 3086, Australia.
B Current address: Department of Medicinal Chemistry, Victorian College of Pharmacy, Monash University, Parkville VIC 3052, Australia.
C Current address: Biolytica Laboratories, Bulleen VIC 3105, Australia.
D Department of Biochemistry, La Trobe University, Bundoora VIC 3086, Australia.
E Corresponding author. Email: a.hughes@latrobe.edu.au
Australian Journal of Chemistry 59(6) 407-414 https://doi.org/10.1071/CH06148
Submitted: 4 May 2006 Accepted: 19 June 2006 Published: 6 July 2006
Abstract
We report the full structural determination of the depsipeptide petriellin A. The absolute configuration of the amino acid residues, N-methyl isoleucine and N-methyl threonine, have been determined by a combination of HPLC and TLC comparison of synthetic Marfey’s derivatives and Marfey’s derivatives of the natural product hydrolysate. The configuration of the chiral centres in these two N-methylated residues was found to be the same as those of the common unmethylated l-amino acids.
Acknowledgements
The authors are grateful to Ms Judy Oliver of the Microbiology Department at La Trobe University for assistance in the culture and growth of the fungus. L.A. and J.D. acknowledge La Trobe University for the provision of post-graduate scholarships. The authors thank the Australian Research Council for the award of Small Research Grants that supported aspects of the work described. The authors thank Dr J. A. Reiss for his assistance with preparation of this manuscript.
[1]
K. K. Lee,
J. B. Gloer,
J. A. Scott,
D. Malloch,
J. Org. Chem. 1995, 60, 5384.
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and references therein.
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