Synthesis of 28-19F-amphotericin B methyl ester

Hiroshi Tsuchikawa; Naohiro Matsushita; Nobuaki Matsumori; Michio Murata; Tohru Oishi

doi:10.1016/j.tetlet.2006.06.159

Synthesis of 28-¹⁹F-amphotericin B methyl ester

Hiroshi Tsuchikawa, Naohiro Matsushita, Nobuaki Matsumori, Michio Murata, Tohru Oishi

Research output: Contribution to journal › Article › peer-review

30 Citations (Scopus)

Abstract

A fluorinated amphotericin B (AmB) derivative, 28-¹⁹F-AmB methyl ester (3), labeled at the polyene moiety, was synthesized by combining chemical synthesis with degradation of a natural product via cross-coupling reactions and macrolactonization. The fluorinated derivative 3 showed antifungal activity similar to that of AmB, and is expected to be a powerful tool for NMR-based investigation of the mechanism of ion-channel formation.

Original language	English
Pages (from-to)	6187-6191
Number of pages	5
Journal	Tetrahedron Letters
Volume	47
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2006.06.159
Publication status	Published - Aug 28 2006
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.06.159

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title = "Synthesis of 28-19F-amphotericin B methyl ester",

abstract = "A fluorinated amphotericin B (AmB) derivative, 28-19F-AmB methyl ester (3), labeled at the polyene moiety, was synthesized by combining chemical synthesis with degradation of a natural product via cross-coupling reactions and macrolactonization. The fluorinated derivative 3 showed antifungal activity similar to that of AmB, and is expected to be a powerful tool for NMR-based investigation of the mechanism of ion-channel formation.",

author = "Hiroshi Tsuchikawa and Naohiro Matsushita and Nobuaki Matsumori and Michio Murata and Tohru Oishi",

note = "Funding Information: We are grateful to Professor Yasuhiro Uozumi and Dr. Hiroaki Sasagawa of the Institute for Molecular Science for measurement of 920 MHz 1 H NMR spectra. This work was supported by Grants-In-Aid for Scientific Research (Nos. 15201048 and 15350024), for Scientific Research in Priority Areas (A) (Nos. 12045243 and 16073211), and for Young Scientists (A) (No. 17681027) from MEXT, Japan. ",

year = "2006",

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doi = "10.1016/j.tetlet.2006.06.159",

language = "English",

volume = "47",

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journal = "Tetrahedron Letters",

issn = "0040-4039",

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T1 - Synthesis of 28-19F-amphotericin B methyl ester

AU - Tsuchikawa, Hiroshi

AU - Matsushita, Naohiro

AU - Matsumori, Nobuaki

AU - Murata, Michio

AU - Oishi, Tohru

N1 - Funding Information: We are grateful to Professor Yasuhiro Uozumi and Dr. Hiroaki Sasagawa of the Institute for Molecular Science for measurement of 920 MHz 1 H NMR spectra. This work was supported by Grants-In-Aid for Scientific Research (Nos. 15201048 and 15350024), for Scientific Research in Priority Areas (A) (Nos. 12045243 and 16073211), and for Young Scientists (A) (No. 17681027) from MEXT, Japan.

PY - 2006/8/28

Y1 - 2006/8/28

N2 - A fluorinated amphotericin B (AmB) derivative, 28-19F-AmB methyl ester (3), labeled at the polyene moiety, was synthesized by combining chemical synthesis with degradation of a natural product via cross-coupling reactions and macrolactonization. The fluorinated derivative 3 showed antifungal activity similar to that of AmB, and is expected to be a powerful tool for NMR-based investigation of the mechanism of ion-channel formation.

AB - A fluorinated amphotericin B (AmB) derivative, 28-19F-AmB methyl ester (3), labeled at the polyene moiety, was synthesized by combining chemical synthesis with degradation of a natural product via cross-coupling reactions and macrolactonization. The fluorinated derivative 3 showed antifungal activity similar to that of AmB, and is expected to be a powerful tool for NMR-based investigation of the mechanism of ion-channel formation.

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DO - 10.1016/j.tetlet.2006.06.159

M3 - Article

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SN - 0040-4039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 35

ER -

Synthesis of 28-¹⁹F-amphotericin B methyl ester

Abstract

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