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Absolute configuration at C45 in 45-hydroxyyessotoxin, a marine polyether toxin isolated from shellfish
A Morohashi1, M Satake, Y Oshima
1Graduate School of Agricultural Science, Tohoku University, Sendai, Japan.
Bioscience, Biotechnology, and Biochemistry
|September 19, 2000
Summary
Researchers identified the marine toxin 45-hydroxyyessotoxin in scallops. Esterification and NMR analysis confirmed the R configuration at the C45 position of this yessotoxin analog.
Area of Science:
- Marine natural products chemistry
- Marine biotoxins
- Organic chemistry
Background:
- Yessotoxin is a marine polyether toxin produced by dinoflagellates.
- Yessotoxin and its analogs can accumulate in shellfish, posing risks to human health.
- The stereochemistry of yessotoxin analogs is crucial for understanding their biological activity.
Purpose of the Study:
- To isolate and characterize 45-hydroxyyessotoxin from the scallop Patinopecten yessoensis.
- To determine the stereochemical configuration at the C45 position of 45-hydroxyyessotoxin.
- To contribute to the understanding of marine toxin structures and their origins.
Main Methods:
- Isolation of 45-hydroxyyessotoxin and yessotoxin from Patinopecten yessoensis.
- Esterification of the C45-hydroxy group using (S)- and (R)-alpha-methoxyalpha-trifluoromethylphenylacetic acids (MTPA).
- Detailed analysis of 2D Nuclear Magnetic Resonance (NMR) spectra of the MTPA esters.
Main Results:
- 45-hydroxyyessotoxin was successfully isolated from the scallop.
- The synthesis of diastereomeric MTPA esters allowed for stereochemical determination.
- 2D NMR analysis unequivocally established the R configuration at the C45 position.
Conclusions:
- The stereochemistry at C45 of 45-hydroxyyessotoxin has been determined as R.
- This finding provides important structural information for marine toxin research.
- Understanding the stereochemistry of marine toxins is vital for toxicological and ecological studies.