Efficient chemoenzymatic oligosaccharide synthesis by reverse phosphorolysis using cellobiose phosphorylase and cellodextrin phosphorylase from Clostridium thermocellum

Nakai, Hiroyuki; Hachem, Maher Abou; Petersen, Bent O.; Westphal, Yvonne; Mannerstedt, Karin; Baumann, Martin; Dilokpimol, Adiphol; Schols, Henk A.; Duus, Jens Øllgaard; Svensson, Birte

doi:10.1016/j.biochi.2010.07.013

Cited by 53 publications

(52 citation statements)

References 55 publications

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“…Ab alance between stability and activity was found for CP at 50 8 8C, retaining over 58% of its initial activity after2 4h,w hile operating at roughly 80% of its maximal velocity. [27] In addition,t he typically very lowa ffinity of disaccharidep hosphorylases for non-carbohydrate acceptors urges the addition of solvents. [28] Therefore,t he half-life (t 50 )o fC Pw as also determined in the presence of some commonly used organic cosolvents,a s well as in some ILs (Table 1).…”

Section: Development Of As Uitable Glycosylation Systemmentioning

confidence: 99%

Chemoenzymatic Synthesis of β‐D‐Glucosides using Cellobiose Phosphorylase from Clostridium thermocellum

et al. 2015

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Over the past decade,d isaccharide phosphorylases have been successfully applied for the synthesiso fn umerous a-glucosides. In contrast, much less researchh as been done with respect to the production of b-glucosides. Although cellobiose phosphorylase was alreadys uccessfully used for the synthesiso fv arious disaccharides and branched trisaccharides,i ts glycosylation potentialt owards small organic compounds has not been explored to date. Unfortunately,d isaccharide phosphorylases typically have av ery low affinity for non-carbohydrate acceptors,w hich urges the addition of solvents.T he ionic liquid AMMOENG TM 101 ande thyl acetate were identifieda st he most promising solvents,a llowing the synthesis of various b-glucosides.N extt oh exyl, heptyl,o ctyl,n onyl, decyl and undecyl b-d-glucopyranosides, also the formation of vanillyl 4-O-b-d-glucopyranoside,2 -phenylethyl b-d-glucopyranoside, bcitronellyl b-d-glucopyranoside and 1-O-b-d-glucopyranosyl hydroquinone was confirmed by nuclear magnetic resonance spectroscopy and mass spectrometry.M oreover, the stability of cellobiose phosphorylase could be drastically improvedb yc reating cross-linked enzyme aggregates,w hilet he efficiency of the biocatalyst for the synthesis of octyl b-d-glucopyranoside wasd oubled by imprinting with octanol. Theu sefulness of the latter system was illustrated by performing three consecutive batch conversions with octanoli mprinted cross-linked enzyme aggregates, yieldingr oughly 2gof octyl b-d-glucopyranoside.

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Section: Development Of As Uitable Glycosylation Systemmentioning

confidence: 99%

Chemoenzymatic Synthesis of β‐D‐Glucosides using Cellobiose Phosphorylase from Clostridium thermocellum

et al. 2015

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“…Feruloyl xylo-oligosaccharides (FeXOSs) were obtained from corn cobs by treatment with a Thermoascus aurantiacus family 10-b-D-endoxylanase (Katapodis and Christakopoulos 2008). Inverting cellobiose phosphorylase and cellodextrin phosphorylase from Clostridium thermocellum ATCC27405 belonging to glycoside hydrolase family 94 catalysed reverse phosphorolysis of a-D-glucose 1-phosphate to produce b-glucosyl oligosaccharides (Nakai et al 2010). In contrast to prolific use of exoglycosidases as oligosaccharide synthesis tool, endoglycosidases have found very studies.…”

Section: Synthesis and Purification Of Oligosaccharidesmentioning

confidence: 99%

“…2)-linked oligosaccharides Kong (2007) Isomerization reaction of lactose Lactulose Zokaee et al(2002) Extraction by water or aqueous methanol or ethanol solutions Raffinose oligosaccharides Mussatto and Mancilha (2007) Hydrolysis of rice bran by trifluoroacetic acid Reverse phosphorolysis of a-Dglucose 1-phosphate by cellobiose phosphorylase and cellodextrin phosphorylase b-Glucosyl oligosaccharides Nakai et al (2010) best because of its precise results, analytical versatility and very high sensitivity. Over the past decade, the fast atom bombardment (FAB) technique has been replaced by the more sensitive techniques of electrospray ionization (ESI) and matrix-assisted laser desorption/ionization (MALDI) (Cmelik and Chmelik 2010).…”

Section: Feruloylatedarabinoxylooligosaccharidesmentioning

confidence: 99%

Functional oligosaccharides: production, properties and applications

Patel

Goyal

2010

World J Microbiol Biotechnol

252

123

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Worldwide interest in oligosaccharides has been increasing ever since they were accorded the prebiotic status. The oligosaccharides of various origin like, bacteria, algae, fungi and higher plants have been used extensively both as food ingredients and pharmacological supplements. The non-digestible oligosaccharides have been implicated as dietary fibre, sweetener, weight controlling agent and humectant in confectioneries, bakeries and breweries. Functional oligosaccharides have been found effective in gastrointestinal normal flora proliferation and pathogen suppression, dental caries prevention, enhancement of immunity, facilitation of mineral absorption, source of antioxidant, antibiotic alternative, regulators of blood glucose in diabetics and serum lipids in hyperlipidemics. Apart from the pharmacological applications, oligosaccharides have found use in drug delivery, cosmetics, animal and fishery feed, agriculture, etc. Keeping in view the importance of the functional oligosaccharides, we present an overview of their natural sources, types, structures, physiological properties. Conventional as well as novel synthesis, purification and analysis methods are summarized. Recent promising developments in this area are presented to facilitate their further exploitation.

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“…32,33 The unique characteristic of the CDP-catalyzed reaction is that CDP has poor substrate specificity against anomeric substitutes of β-Dglucosyl primers. 24,27 Indeed, various primers, such as β-linked disaccharides, 34,35 β-glycosyl antioxidants, 36 and cellobiosylated dendrimers, 37 were employed in the reaction to obtain terminus-functionalized cellulose oligomers as water-soluble products. In our previous work, sheet-like nanocelluloses with numerous azide groups on the surfaces were successfully synthesized via the oligomerization of αG1P monomers from β-glucosyl azide primers, thus demonstrating the surfacefunctionalization of nanocelluloses through copper(I)-catalyzed Huisgen cycloaddition reactions.…”

Section: ■ Introductionmentioning

confidence: 99%

Enzymatic Synthesis of Oligo(ethylene glycol)-Bearing Cellulose Oligomers for in Situ Formation of Hydrogels with Crystalline Nanoribbon Network Structures

et al. 2016

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Enzymatic synthesis of cellulose and its derivatives has gained considerable attention for use in the production of artificial crystalline nanocelluloses with unique structural and functional properties. However, the poor colloidal stability of the nanocelluloses during enzymatic synthesis in aqueous solutions limits their crystallization-based self-assembly to greater architectures. In this study, oligo(ethylene glycol) (OEG)-bearing cellulose oligomers with different OEG chain lengths were systematically synthesized via cellodextrin phosphorylase-catalyzed oligomerization of α-d-glucose l-phosphate monomers against OEG-bearing β-d-glucose primers. The products were self-assembled into extremely well-grown crystalline nanoribbon network structures with the cellulose II allomorph, potentially due to OEG-derived colloidal stability of the nanoribbon's precursors, followed by the in situ formation of physically cross-linked hydrogels. The monomer conversions, average degree of polymerization, and morphologies of the nanoribbons changed significantly, depending on the OEG chain length. Taken together, our findings open a new avenue for the enzymatic reaction-based facile production of novel cellulosic soft materials with regular nanostructures.

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Efficient chemoenzymatic oligosaccharide synthesis by reverse phosphorolysis using cellobiose phosphorylase and cellodextrin phosphorylase from Clostridium thermocellum

Cited by 53 publications

References 55 publications

Chemoenzymatic Synthesis of β‐D‐Glucosides using Cellobiose Phosphorylase from Clostridium thermocellum

Chemoenzymatic Synthesis of β‐D‐Glucosides using Cellobiose Phosphorylase from Clostridium thermocellum

Functional oligosaccharides: production, properties and applications

Enzymatic Synthesis of Oligo(ethylene glycol)-Bearing Cellulose Oligomers for in Situ Formation of Hydrogels with Crystalline Nanoribbon Network Structures

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