Studies on Chemical Modification of Monensin IX. Synthesis of 26-Substituted Monensins and Their Na+ Ion Transport Activity

Rie TANAKA; Akito NAGATSU; Hajime MIZUKAMI; Yukio OGIHARA; Jinsaku SAKAKIBARA

doi:10.1248/cpb.49.711

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Studies on Chemical Modification of Monensin IX. Synthesis of 26-Substituted Monensins and Their Na⁺ Ion Transport Activity

Rie TANAKA, Akito NAGATSU, Hajime MIZUKAMI, Yukio OGIHARA, Jinsaku SAKAKIBARA

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Keywords: C-26 modified monensin, sodium ion transport activity, antibacterial activity, 26-phenylaminomonensin

JOURNAL FREE ACCESS

2001 Volume 49 Issue 6 Pages 711-715

DOI https://doi.org/10.1248/cpb.49.711

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Abstract

The C-26 modified monensin derivatives, 26-O-benzoylmonensin (3), 26-O-benzylmonensin (4) and 26-phenylaminomonensin (5) were prepared from monensin (1). Na⁺ ion transport activity through biological membrane and antibacterial activity of 3-5 were evaluated and compared with the activities reported for a 26-phenylurethane derivative (2). Among these compounds, 5 showed the largest Na⁺ ion transport and antibacterial activities. In these compounds, the formation of head-to-tail hydrogen bonds was suggested to be an important factor for Na⁺ ion transport and antibacterial activities.

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