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Configuration of the psymberin amide side chain
Sezgin Kiren1, Lawrence J Williams
1Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, 08854, USA.
Organic Letters
|July 1, 2005
Summary
Researchers elucidated the amide side chain structure of psymberin, a potent cytotoxin. X-ray crystallography and NMR data confirmed the anti configuration of the natural product
Area of Science:
- Natural Product Chemistry
- Organic Chemistry
- Structural Biology
Background:
- Psymberin is a potent and selective cytotoxin.
- The precise structure of its amide side chain was previously undetermined.
- Elucidating this structure is crucial for understanding its biological activity.
Purpose of the Study:
- To propose and confirm the structure of the amide side chain of psymberin.
- To synthesize syn and anti isomers of the amide side chain for comparison.
- To establish the stereochemical configuration of psymberin's amide side chain.
Main Methods:
- Synthesis of syn and anti amide side chain models.
- X-ray crystallographic analysis of the anti isomer.
- Comparison of 1H and 13C Nuclear Magnetic Resonance (NMR) data.
Main Results:
- The anti configuration of the amide side chain was confirmed by X-ray crystallography.
- NMR data showed homology between psymberin and the synthetic anti isomer.
- The syn isomer did not show homology with the natural product.
Conclusions:
- The amide side chain of psymberin possesses an anti configuration.
- This structural determination provides a basis for further studies on psymberin's mechanism of action.
- The synthetic models are valuable tools for structural elucidation of related natural products.