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Antibiotic A 19009. Structural investigation and synthesis
The Journal of Antibiotics
|July 1, 1983
Summary
The structure of fermentation product A 19009 was determined to be N2-L-alanyl-N3-fumaramoyl-L-2,3-diaminopropanoic acid. This compound shows significantly lower activity against Trichomonas vaginalis compared to its isomer.
Area of Science:
- Biochemistry
- Organic Chemistry
- Microbiology
Background:
- Fermentation product A 19009 was previously assigned an incorrect structure.
- Understanding the precise chemical structure is crucial for biological activity assessment.
Purpose of the Study:
- To elucidate the correct structure of fermentation product A 19009.
- To compare the biological activity of the correct structure with the previously proposed one.
Main Methods:
- Nuclear Magnetic Resonance (NMR) spectroscopy (13C and 1H) was employed for structural reinvestigation.
- Independent chemical synthesis was performed to confirm the proposed structure.
Main Results:
- The structure was established as N2-L-alanyl-N3-fumaramoyl-L-2,3-diaminopropanoic acid (2).
- This confirmed structure is isomeric to the originally proposed structure (1).
- Compound 2 exhibited very low activity against Trichomonas vaginalis, unlike compound 1.
Conclusions:
- The chemical structure of fermentation product A 19009 has been corrected.
- The corrected structure possesses significantly reduced anti-Trichomonas vaginalis activity.