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Environmentally benign glycosylation of aryl pyranosides and aryl/alkyl furanosides demonstrating the versatility of thermostable CGTase from Thermoanaerobacterium sp.

Abstract : An extensive study on the specificity of transglycosylation and disproportionation of Thermoanaerobacterium sp. cyclodextrin glucosyltranferases against aryl glucopyranosides or furanosides was achieved. While a mixture of maltoside and isomaltoside was obtained respectively using p-nitrophenyl glucopyranoside as acceptor, only one regioisomer, namely the p-nitrophenyl α-D-Glcp-(1,3)-α-L-Araf was isolated using p-nitrophenyl arabinofuranoside as acceptor. Interestingly, similar outcomes were found when using p-nitrophenyl galactofuranoside. Furthermore, activation by microwave irradiation resulted in faster reaction times and higher yields and led to glucosidic oligosaccharides with up to 70% conversion. The influence of the anomeric and C-4 configurations of the glycosidic acceptors on the transglycosylation, previously stated for the CGTase family, was not observed and unconventional substrate specificity towards alkyl furanosides was highlighted.
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Submitted on : Monday, October 20, 2014 - 9:53:39 AM
Last modification on : Thursday, May 28, 2020 - 3:32:01 PM
Long-term archiving on: : Wednesday, January 21, 2015 - 10:31:15 AM

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Alizé Pennec, Laurent Legentil, Luis Herrera-Estrella, Vincent Ferrières, Anne-Laure Chauvin, et al.. Environmentally benign glycosylation of aryl pyranosides and aryl/alkyl furanosides demonstrating the versatility of thermostable CGTase from Thermoanaerobacterium sp.. Green Chemistry, Royal Society of Chemistry, 2014, 16, pp.3803. ⟨10.1039/C4GC00631C⟩. ⟨hal-01075732⟩

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