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Conformational studies of nikkomycin X in aqueous solution
E Krainer1, F Naider, J M Becker
1Department of Chemistry, College of Staten Island, New York 10301.
Biopolymers
|July 5, 1990
Summary
Nikkomycin X, an antifungal antibiotic, exhibits a flexible structure in water. Its nucleoside moiety exists in both syn and anti forms, with ribose conformation shifting slightly with pH changes.
Area of Science:
- Biochemistry
- Structural Biology
- Medicinal Chemistry
Background:
- Nikkomycin X is a peptidyl-nucleoside antibiotic.
- It functions by inhibiting chitin synthesis in fungi.
- Understanding its aqueous conformation is crucial for drug development.
Purpose of the Study:
- To elucidate the conformational properties of Nikkomycin X in aqueous solution.
- To investigate the influence of pH on Nikkomycin X conformation.
Main Methods:
- Utilized pH titration studies monitoring NMR shifts of exchangeable and nonexchangeable protons.
- Applied Nuclear Overhauser Effect (NOE) experiments.
- Analyzed ribose ring conformation using a two-state model.
Main Results:
- Nikkomycin X displays an unfolded or conformationally flexible structure in aqueous solution.
- Both syn and anti conformations of the nucleoside moiety were observed to coexist.
- A minor shift in ribose ring conformation from N-type to S-type occurred between pH 1 and 6.
Conclusions:
- Nikkomycin X possesses a dynamic and flexible structure in aqueous environments.
- The coexistence of nucleoside conformations and pH-dependent ribose shifts are key structural features.
- These findings provide insights into the molecular behavior of Nikkomycin X relevant to its antifungal activity.