Synthesis of 28- 19 F-amphotericin B methyl ester

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

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

A fluorinated amphotericin B (AmB) derivative, 28- 19 F-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 languageEnglish
Pages (from-to)6187-6191
Number of pages5
JournalTetrahedron Letters
Volume47
Issue number35
DOIs
Publication statusPublished - Aug 28 2006
Externally publishedYes

Fingerprint

Amphotericin B
Derivatives
Polyenes
Cross Reactions
Biological Products
Ion Channels
Nuclear magnetic resonance
Degradation
methylamphotericin B

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Synthesis of 28- 19 F-amphotericin B methyl ester . / Tsuchikawa, Hiroshi; Matsushita, Naohiro; Matsumori, Nobuaki; Murata, Michio; Oishi, Tohru.

In: Tetrahedron Letters, Vol. 47, No. 35, 28.08.2006, p. 6187-6191.

Research output: Contribution to journalArticle

Tsuchikawa, Hiroshi ; Matsushita, Naohiro ; Matsumori, Nobuaki ; Murata, Michio ; Oishi, Tohru. / Synthesis of 28- 19 F-amphotericin B methyl ester In: Tetrahedron Letters. 2006 ; Vol. 47, No. 35. pp. 6187-6191.
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