title: A straightforward access to TMG-chitooligomycins and their evaluation as β-N-acetylhexosaminidase inhibitors.
abstract: A chemo-biotechnological approach is reported for the synthesis of TMG-chitooligomycins, CO-n (NMe(3)). Their abilities to inhibit β-N-acetylhexosaminidases (HexNAcases), from Aspergillus oryzae (AoHex, fungi), Canavalia ensiformis (CeHex, plant) HexNAcases and a chitobiase from Serratia marcescens (SmCHB, bacteria) were studied and compared with their precursors CO-n (N). CO-n (NMe(3)) were revealed as potent inhibitors for AoHex and SmCHB with a proved chain length effect while CO-n (N) was a highly selective inhibitor of SmCHB. This route can be considered as the privileged way to produce easily and in large scale a wide range of size-defined chitooligosaccharide-based inhibitors to fine-tune the structure-activity relationships for inhibition of HexNAcases from various origins.
authors: Centre de Recherches sur les Macromolécules Végétales CERMAV-CNRS (Affiliated with Université Joseph Fourier, and Member of the Institut de Chimie Moléculaire de Grenoble), BP 53, 38041 Grenoble cedex 9, France. sami.halila@cermav.cnrs.fr
authors: Sami
authors: S
authors: Halila
authors: Eric
authors: E
authors: Samain
authors: Constantin E
authors: CE
authors: Vorgias
authors: Sylvie
authors: S
authors: Armand
mesh_terms: D000118:Acetylglucosaminidase / Q000378:metabolism; D001236:Aspergillus oryzae / Q000201:enzymology; D032449:Canavalia / Q000201:enzymology; D004789:Enzyme Activation / Q000187:drug effects; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000378:metabolism*; D013329:Structure-Activity Relationship; D013402:Sugar Alcohols / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001619:beta-N-Acetylhexosaminidases / Q000378:metabolism*
chemical_list: D004791:Enzyme Inhibitors; D013402:Sugar Alcohols; C528826:TMG-chitotriomycin; D006026:Glycoside Hydrolases; D000118:Acetylglucosaminidase; D001619:beta-N-Acetylhexosaminidases