title: TMG-chitotriomycin as a probe for the prediction of substrate specificity of β-N-acetylhexosaminidases.
abstract: TMG-chitotriomycin (1) produced by the actinomycete Streptomyces annulatus NBRC13369 was examined as a probe for the prediction of substrate specificity of β-N-acetylhexosaminidases (HexNAcases). According to the results of inhibition assays, 14 GH20 HexNAcases from various organisms were divided into 1-sensitive and 1-insensitive enzymes. Three representatives of each group were investigated for their substrate specificity. The 1-sensitive HexNAcases hydrolyzed N-acetylchitooligosaccharides but not N-glycan-type oligosaccharides, whereas the 1-insensitive enzymes hydrolyzed N-glycan-type oligosaccharides but not N-acetylchitooligosaccharides, indicating that TMG-chitotriomycin can be used as a molecular probe to distinguish between chitin-degrading HexNAcases and glycoconjugate-processing HexNAcases.
authors.affiliation: Laboratory of Bioresources Chemistry, The Graduate School of Environmental & Life Science, Okayama University, Kita-ku, Okayama, Japan.
authors.forename: Hiroto
authors.initials: H
authors.lastname: Shiota
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Kanzaki
authors.forename: Tadashi
authors.initials: T
authors.lastname: Hatanaka
authors.forename: Teruhiko
authors.initials: T
authors.lastname: Nitoda
mesh_terms: D002236:Carbohydrate Conformation; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D015335:Molecular Probes / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013379:Substrate Specificity / Q000187:drug effects; D013402:Sugar Alcohols / Q000737:chemistry / Q000494:pharmacology*; D001619:beta-N-Acetylhexosaminidases / Q000037:antagonists & inhibitors* / Q000302:isolation & purification / Q000378:metabolism
chemical_list: D004791:Enzyme Inhibitors; D015335:Molecular Probes; D013402:Sugar Alcohols; C528826:TMG-chitotriomycin; D001619:beta-N-Acetylhexosaminidases