A straightforward access to TMG-chitooligomycins and their evaluation as β-N-acetylhexosaminidase inhibitors

[Display omitted] ► Chemo-biotechnological approach is described for access to TMG-chitooligomycins. ► CO-n (NMe3) and CO-n (N) were studied as HexNAcase inhibitors. ► The N-methyl quaternization as well as chitin chain length effect was studied. A chemo-biotechnological approach is reported for the...

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Bibliographic Details
Published in:Carbohydrate research 2013-03, Vol.368, p.52-56
Main Authors: Halila, Sami, Samain, Eric, Vorgias, Constantin E., Armand, Sylvie
Format: Article
Language:English
Subjects:
Acetylglucosaminidase - metabolism
Aspergillus oryzae
Aspergillus oryzae - enzymology
bacteria
beta-N-acetylhexosaminidase
beta-N-Acetylhexosaminidases - metabolism
Biotechnology
Canavalia - enzymology
Canavalia ensiformis
Chitooligosaccharides
Enzyme Activation - drug effects
Enzyme Inhibitors - chemical synthesis
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - pharmacology
fungi
Glycoside Hydrolases - metabolism
Hexosaminidase
Inhibitors
N-Quaternization
Serratia marcescens
Structure-Activity Relationship
structure-activity relationships
Sugar Alcohols - chemical synthesis
Sugar Alcohols - chemistry
Sugar Alcohols - pharmacology
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Summary:[Display omitted] ► Chemo-biotechnological approach is described for access to TMG-chitooligomycins. ► CO-n (NMe3) and CO-n (N) were studied as HexNAcase inhibitors. ► The N-methyl quaternization as well as chitin chain length effect was studied. A chemo-biotechnological approach is reported for the synthesis of TMG-chitooligomycins, CO-n (NMe3). 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 (NMe3) 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.
ISSN:0008-6215
1873-426X
0008-6215
DOI:10.1016/j.carres.2012.12.007