SYNTHESIS AND ANTIFUNGAL ACTIVITY OF PRADIMICIN DERIVATIVES MODIFICATIONS OF THE SUGAR PART

SHIMPEI ABURAKI; HARUHIRO YAMASHITA; TAKESHI OHNUMA; HAJIME KAMACHI; TOSHIO MORIYAMA; SHINJI MASUYOSHI; HIDEO KAMEI; MASATAKA KONISHI; TOSHIKAZU OKI

doi:10.7164/antibiotics.46.631

SYNTHESIS AND ANTIFUNGAL ACTIVITY OF PRADIMICIN DERIVATIVES

MODIFICATIONS OF THE SUGAR PART

SHIMPEI ABURAKI, HARUHIRO YAMASHITA, TAKESHI OHNUMA, HAJIME KAMACHI, TOSHIO MORIYAMA, SHINJI MASUYOSHI, HIDEO KAMEI, MASATAKA KONISHI, TOSHIKAZU OKI

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JOURNAL FREE ACCESS

1993 Volume 46 Issue 4 Pages 631-640

DOI https://doi.org/10.7164/antibiotics.46.631

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Abstract

Modifications at the sugar part of pradimicins were carried out by glycosidations of the aglycones or chemical transformations of natural pradimicins and their antifungal activity was evaluated. Among them, some of the D-xylose-modified derivatives (14, 17, 24) showed activity comparable to that of pradimicin A. The structure-activity relationships obtained through there sutdies clarified the role of the sugar part in the manifestation of antifungal activity: The 5-O-(6-deoxy-β-D-sugar) is essential for activity and 2'-epi, 3'-oxo and 4'-deoxy sugar derivatives retain activity against yeasts.

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