Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase

Gonzalez, Jose L. Ugia; Rodrigo-Frutos, David; Belmonte-Reche, Efres; Peñalver, Pablo; Poveda, Ana; Jiménez‐Barbero, Jesús; Ballesteros, Antonio; Hirose, Yoshio; Polaina, Julio; Morales, Juan Carlos; Fernández-Lobato, María; Plou, Francisco J.

doi:10.3390/molecules23061271

Cited by 21 publications

(33 citation statements)

References 54 publications

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“…The glycosylation of phenolic antioxidants is being exploited as a tool to improve their bioavailability, aqueous solubility and stability, among other properties ,. In fact, many polyphenols naturally occur as glycosides and glycoconjugates, in which the glycone moiety often exerts a great influence in their activity .…”

Section: Introductionmentioning

confidence: 99%

Fructosylation of Hydroxytyrosol by the β‐Fructofuranosidase from Xanthophyllomyces dendrorhous: Insights into the Molecular Basis of the Enzyme Specificity

et al. 2018

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This work investigates the ability of the b-fructofuranosidase pXd-INV from the yeast Xanthophyllomyces dendrorhous to glycosylate the olive biophenol hydroxytyrosol (HT). Two fructosylated derivatives (Fru-HT1 and Fru-HT2) were synthesized. Under the best conditions (300 mg/mL sucrose, 25 mg/ mL HT), the maximum yield was 45.6 %. MS and 2D-NMR analyses showed that the major product (Fru-HT1) was fructosylated at the primary OH of HT. The structure of the complexes with the substrates and the product analyzed by crystallography led to the understanding of the molecular determinants regulating the enzymatic mechanism. Product-soaked crystals revealed that the minor derivative (Fru-HT2) was fructosylated at the phenolic p-OH group. The two binding modes for HT at pXd-INV active site are governed almost exclusively by packing to Trp105 (Fru-HT1) and polar interactions with the loop Glu334-Asn342 (Fru-HT2), respectively. Specific mutagenesis at these residues was accomplished to tune the enzyme regiospecificity. One of the studied mutants (N342Q) was notably more specific for the fructosylation at the phenolic OH than the wildtype.

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Section: Introductionmentioning

confidence: 99%

Fructosylation of Hydroxytyrosol by the β‐Fructofuranosidase from Xanthophyllomyces dendrorhous: Insights into the Molecular Basis of the Enzyme Specificity

et al. 2018

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“…(Toruzyme 3.0L) [ 30 , 33 ], employing partially hydrolyzed starch (maltodextrins with DP ≤ 60) as glucosyl donor. This enzyme has demonstrated an extraordinary ability to glucosylate other mono- and polyphenolic compounds [ 26 , 31 , 32 , 34 , 35 , 36 , 37 , 38 ].…”

Section: Resultsmentioning

confidence: 99%

“…In this work, we describe the enzymatic synthesis of an α-glucosylated derivative of hesperetin by a transglycosylation reaction catalyzed by a transglycosidase, namely cyclodextrin glycosyltransferase (CGTase, EC 2.4.1.19), which employs a renewable and easily available carbohydrate (starch) as glucosyl donor [ 30 ]. In previous works, we successfully achieved the α-glucosylation of a flavonoid (epigallocatechin gallate [ 26 ]) and two stilbenes (resveratrol [ 31 ], pterostilbene [ 32 ]) with this enzyme.…”

Section: Introductionmentioning

confidence: 99%

Optimization of Regioselective α-Glucosylation of Hesperetin Catalyzed by Cyclodextrin Glucanotransferase

et al. 2018

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The regioselective α-glucosylation of hesperetin was achieved by a transglycosylation reaction catalyzed by cyclodextrin glucanotransferase (CGTase) from Thermoanaerobacter sp. using soluble starch as glucosyl donor. By combining mass spectrometry (ESI-TOF) and 2D-NMR analysis, the main monoglucosylated derivative was fully characterized (hesperetin 7-O-α-d-glucopyranoside). In order to increase the yield of monoglucoside, several reaction parameters were optimized: Nature and percentage of cosolvent, composition of the aqueous phase, glucosyl donor, temperature, and the concentrations of hesperetin and soluble starch. Under the optimal conditions, which included the presence of 30% of bis(2-methoxyethyl) ether as cosolvent, the maximum concentration of monoglucoside was approximately 2 mM, obtained after 24 h of reaction. To our knowledge, this is the first report of direct glucosylation of hesperetin employing free enzymes instead of whole cells.

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“…Unfortunately, one of the main drawbacks of CGTases is that their product selectivity is not very high, because the enzyme displays its four activities simultaneously [19]. Furthermore, the formation of a homologous series of polyglucosylated products is normally described with this enzyme [20][21][22]. As a result, a low yield of the desired glycosylated product is typically obtained [23].…”

Section: Introductionmentioning

confidence: 99%

“…Typical cosolvents for transglycosylation reactions include acetonitrile, DMSO, ethers, tertiary alcohols, etc. [22,23,36], and more recently, biomass-derived solvents and ionic liquids [37,38].…”

Section: Introductionmentioning

confidence: 99%

Production and Surfactant Properties of Tert-Butyl α-d-Glucopyranosides Catalyzed by Cyclodextrin Glucanotransferase

et al. 2019

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While testing the ability of cyclodextrin glucanotransferases (CGTases) to glucosylate a series of flavonoids in the presence of organic cosolvents, we found out that this enzyme was able to glycosylate a tertiary alcohol (tert-butyl alcohol). In particular, CGTases from Thermoanaerobacter sp. and Thermoanaerobacterium thermosulfurigenes EM1 gave rise to the appearance of at least two glycosylation products, which were characterized by mass spectrometry (MS) and nuclear magnetic resonance (NMR) as tert-butyl-α-D-glucoside (major product) and tert-butyl-α-D-maltoside (minor product). Using partially hydrolyzed starch as glucose donor, the yield of transglucosylation was approximately 44% (13 g/L of tert-butyl-α-D-glucoside and 4 g/L of tert-butyl-α-D-maltoside). The synthesized tert-butyl-α-D-glucoside exhibited the typical surfactant behavior (critical micellar concentration, 4.0–4.5 mM) and its properties compared well with those of the related octyl-α-D-glucoside. To the best of our knowledge, this is the first description of an enzymatic α-glucosylation of a tertiary alcohol.

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Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase

Cited by 21 publications

References 54 publications

Fructosylation of Hydroxytyrosol by the β‐Fructofuranosidase from Xanthophyllomyces dendrorhous: Insights into the Molecular Basis of the Enzyme Specificity

Fructosylation of Hydroxytyrosol by the β‐Fructofuranosidase from Xanthophyllomyces dendrorhous: Insights into the Molecular Basis of the Enzyme Specificity

Optimization of Regioselective α-Glucosylation of Hesperetin Catalyzed by Cyclodextrin Glucanotransferase

Production and Surfactant Properties of Tert-Butyl α-d-Glucopyranosides Catalyzed by Cyclodextrin Glucanotransferase

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