TMG-chitotriomycin, an enzyme inhibitor specific for insect and fungal β-N-acetylglucosaminidases, produced by actinomycete Streptomyces anulatus NBRC 13369

Hirokazu Usuki, Teruhiko Nitoda, Misato Ichikawa, Nahoko Yamaji, Takashi Iwashita, Hajime Komura, Hiroshi Kanzaki

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

A novel β-N-acetylglucosaminidase (GlcNAcase) inhibitor named TMG-chitotriomycin (1) was isolated from the culture filtrate of Streptomyces anulatus NBRC13369. The strain produced 1 only when colloidal chitin was used as the sole carbon source in the production medium. The structure of 1 was determined by spectral and constitutive sugar analyses of the corresponding alditol derivatives to be an equilibrated mixture of α-D-N,N,N- triMeGlcNH2-(1,4)-β-D-GlcNAc-(1,4)-β-D-GlcNAc-(1,4)-D- GlcNAc and its C-2 epimer of the reducing end residue. TMG-chitotriomycin (1) showed potent and selective inhibition of insect and fungal GlcNAcases with no inhibition of mammalian and plant GlcNAcases. In contrast, the known GlcNAcase inhibitor nagstatin potently inhibited all GlcNAcases. It should be emphasized that synthesized D-N,N,N-triMeGlcNH2, which is the component sugar of 1, showed no inhibition of the insect Spodoptera litura GlcNAcase. These results suggest that the (GlcNAc)3 unit positioned at the reducing end of 1 is essential for its enzyme inhibitory activity. The unique inhibitory spectrum of 1 will be useful to study chitinolytic systems and to develop selective fungicides or pesticides.

Original languageEnglish
Pages (from-to)4146-4152
Number of pages7
JournalJournal of the American Chemical Society
Volume130
Issue number12
DOIs
Publication statusPublished - Mar 26 2008

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Acetylglucosaminidase
Actinobacteria
Streptomyces
Enzyme Inhibitors
Sugars
Insects
Enzymes
Sugar Alcohols
Fungicides
Spodoptera
Chitin
Enzyme activity
Pesticides
Carbon
Derivatives
TMG-chitotriomycin
2-acetamido-2-deoxy-4-O-(beta-2-acetamid-2-deoxyglucopyranosyl)glucopyranose
N-acetylglucopyranosylamine
nagstatin

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

TMG-chitotriomycin, an enzyme inhibitor specific for insect and fungal β-N-acetylglucosaminidases, produced by actinomycete Streptomyces anulatus NBRC 13369. / Usuki, Hirokazu; Nitoda, Teruhiko; Ichikawa, Misato; Yamaji, Nahoko; Iwashita, Takashi; Komura, Hajime; Kanzaki, Hiroshi.

In: Journal of the American Chemical Society, Vol. 130, No. 12, 26.03.2008, p. 4146-4152.

Research output: Contribution to journalArticle

Usuki, Hirokazu ; Nitoda, Teruhiko ; Ichikawa, Misato ; Yamaji, Nahoko ; Iwashita, Takashi ; Komura, Hajime ; Kanzaki, Hiroshi. / TMG-chitotriomycin, an enzyme inhibitor specific for insect and fungal β-N-acetylglucosaminidases, produced by actinomycete Streptomyces anulatus NBRC 13369. In: Journal of the American Chemical Society. 2008 ; Vol. 130, No. 12. pp. 4146-4152.
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abstract = "A novel β-N-acetylglucosaminidase (GlcNAcase) inhibitor named TMG-chitotriomycin (1) was isolated from the culture filtrate of Streptomyces anulatus NBRC13369. The strain produced 1 only when colloidal chitin was used as the sole carbon source in the production medium. The structure of 1 was determined by spectral and constitutive sugar analyses of the corresponding alditol derivatives to be an equilibrated mixture of α-D-N,N,N- triMeGlcNH2-(1,4)-β-D-GlcNAc-(1,4)-β-D-GlcNAc-(1,4)-D- GlcNAc and its C-2 epimer of the reducing end residue. TMG-chitotriomycin (1) showed potent and selective inhibition of insect and fungal GlcNAcases with no inhibition of mammalian and plant GlcNAcases. In contrast, the known GlcNAcase inhibitor nagstatin potently inhibited all GlcNAcases. It should be emphasized that synthesized D-N,N,N-triMeGlcNH2, which is the component sugar of 1, showed no inhibition of the insect Spodoptera litura GlcNAcase. These results suggest that the (GlcNAc)3 unit positioned at the reducing end of 1 is essential for its enzyme inhibitory activity. The unique inhibitory spectrum of 1 will be useful to study chitinolytic systems and to develop selective fungicides or pesticides.",
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