A chemo-enzymatic pathway to expand cellooligosaccharide chemical space through amine bond introduction.

Autor: Maccow A; Biotechnology Institute (TBI), Université de Toulouse, CNRS, INRAE, INSA, 135 Avenue de Rangueil, CEDEX 04, F-31077 Toulouse, France., Kulyk H; Biotechnology Institute (TBI), Université de Toulouse, CNRS, INRAE, INSA, 135 Avenue de Rangueil, CEDEX 04, F-31077 Toulouse, France; MetaboHUB-MetaToul, National Infrastructure of Metabolomics and Fluxomics, France. Electronic address: hbarbier@insa-toulouse.fr., Severac E; Biotechnology Institute (TBI), Université de Toulouse, CNRS, INRAE, INSA, 135 Avenue de Rangueil, CEDEX 04, F-31077 Toulouse, France. Electronic address: e_severa@insa-toulouse.fr., Morel S; Biotechnology Institute (TBI), Université de Toulouse, CNRS, INRAE, INSA, 135 Avenue de Rangueil, CEDEX 04, F-31077 Toulouse, France. Electronic address: sandrine.morel@insa-toulouse.fr., Moulis C; Biotechnology Institute (TBI), Université de Toulouse, CNRS, INRAE, INSA, 135 Avenue de Rangueil, CEDEX 04, F-31077 Toulouse, France. Electronic address: claire.moulis@insa-toulouse.fr., Boissonnat G; PILI, 226 rue Saint Denis, 75002 Paris, France. Electronic address: guillaume.boissonnat@pili.bio., Remaud-Simeon M; Biotechnology Institute (TBI), Université de Toulouse, CNRS, INRAE, INSA, 135 Avenue de Rangueil, CEDEX 04, F-31077 Toulouse, France. Electronic address: remaud@insa-toulouse.fr., Guieysse D; Biotechnology Institute (TBI), Université de Toulouse, CNRS, INRAE, INSA, 135 Avenue de Rangueil, CEDEX 04, F-31077 Toulouse, France. Electronic address: guieysse@insa-toulouse.fr.
Jazyk: angličtina
Zdroj: Carbohydrate polymers [Carbohydr Polym] 2024 Aug 15; Vol. 338, pp. 122168. Date of Electronic Publication: 2024 Apr 21.
DOI: 10.1016/j.carbpol.2024.122168
Abstrakt: Enzymatic functionalization of oligosaccharides is a useful and environmentally friendly way to expand their structural chemical space and access to a wider range of applications in the health, food, feed, cosmetics and other sectors. In this work, we first tested the laccase/TEMPO system to generate oxidized forms of cellobiose and methyl β-D-cellobiose, and obtained high yields of novel anionic disaccharides (>60 %) at pH 6.0. Laccase/TEMPO system was then applied to a mix of cellooligosaccharides and to pure D-cellopentaose. The occurrence of carbonyl and carboxyl groups in the oxidation products was shown by LC-HRMS, MALDI-TOF and reductive amination of the carbonyl groups was attempted with p-toluidine a low molar mass amine to form the Schiff base, then reduced by 2-picoline borane to generate a more stable amine bond. The new grafted products were characterized by LC-HRMS, LC-UV-MS/MS and covalent grafting was evidenced. Next, the same procedure was adopted to successfully graft a dye, the rhodamine 123, larger in size than toluidine. This two-step chemo-enzymatic approach, never reported before, for functionalization of oligosaccharides, offers attractive opportunities to anionic cellooligosaccharides and derived glucoconjugates of interest for biomedical or neutraceutical applications. It also paves the way for more environmentally-friendly cellulose fabric staining procedures.
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2024 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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