Enzymatic synthesis of primeverosides using transfer reaction by Trichoderma longibrachiatum xylanase |
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Authors: | N. Kadi J. Crouzet |
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Affiliation: | UMR Ingenierie Des Réactions Biologiques-Bioproduction CC 23, Université de Montpellier II, Place E. Bataillon, 34095 Montpellier Cedex 05, France |
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Abstract: | Enzymatic synthesis of two phenyl xylopyranosyl glucopyranosides, through transfer reaction by Trichoderma longibrachiatum endoxylanase, was achieved in the presence of n-hexane used as solvent, phenyl glucoside (10 mM) as acceptor and xylan (2 g/l) as donor. Kinetic study showed that only one compound, identified by 1H and 13C NMR and heteronuclear 2D (1H–13C) chemical shift correlation as phenyl primeveroside (phenyl 6-O-β-xylopyranosyl-1-β-d-glucopyranoside), was synthesized when the reaction time was beyond 1 h. Benzyl and hexyl primeverosides were obtained under the same conditions. When several phenyl glucoside concentrations, from 5 to 50 mM, were used with 2 g/l of xylan, a phenyl primeveroside isomer, identified as phenyl 4-O-β-xylopyranosyl-β-d-glucopyranoside, accumulated in the medium whereas the production of phenyl primeveroside decreased. Only phenyl primeveroside was produced when several xylan concentrations from 2 to 10 g/l were used with 10 mM of phenyl glucoside and its concentration in the reaction mixture increased with the increase of xylan concentration. |
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Keywords: | Disaccharide glycosides Primeverosides Enzymatic synthesis Xylanase Transfer reaction Kinetics FAB+ 1H and 13C NMR |
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