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<p>Allosamidin is a metabolite produced by <i>Streptomyces</i> species, known for its inhibitory activity against family 18 chitinases. All known natural congeners of allosamidin are pseudotrisaccharides featuring a cyclopentane moiety fused with an aminooxazoline ring. We discovered a novel allosamidin congener produced by <i>Streptomyces</i> sp. No. 1-5-6, an allosamidin producer newly isolated from soil. Although its yield was very low, its structure was elucidated by NMR and MS analyses as <i>N</i>-acetylallosaminylallosamidin, the first natural allosamidin congener with a pseudotetrasaccharide structure. <i>N</i>-Acetylallosaminylallosamidin inhibited bacterially expressed mouse acidic mammalian chitinase with an IC₅₀ value of 102.3 nM, showing strong activity, albeit slightly weaker than that of allosamidin.</p>

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Isolation of N-acetylallosaminylallosamidin, a new pseudotetrasaccharide allosamidin congener

  • 期刊论文

  • 发表日期：

    2026年2月25日

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  • Shohei Sakuda,
  • Kenichi Uchida,
  • Noriko Hakoshima,
  • Gota Arakawa,
  • Yuito Saito,
  • Hikaru Honma,
  • Xiaokang Zhang,
  • Tomohiro Furukawa,
  • Kazuo Furihata

摘要

Allosamidin is a metabolite produced by Streptomyces species, known for its inhibitory activity against family 18 chitinases. All known natural congeners of allosamidin are pseudotrisaccharides featuring a cyclopentane moiety fused with an aminooxazoline ring. We discovered a novel allosamidin congener produced by Streptomyces sp. No. 1-5-6, an allosamidin producer newly isolated from soil. Although its yield was very low, its structure was elucidated by NMR and MS analyses as N-acetylallosaminylallosamidin, the first natural allosamidin congener with a pseudotetrasaccharide structure. N-Acetylallosaminylallosamidin inhibited bacterially expressed mouse acidic mammalian chitinase with an IC₅₀ value of 102.3 nM, showing strong activity, albeit slightly weaker than that of allosamidin.