Novel reaction systems for the synthesis of O-glucosides by enzymatic reverse hydrolysis

Balogh, Teréz; Boross, L.; Kosary, J.

doi:10.1016/j.tet.2003.10.098

Cited by 14 publications

(7 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the latter case the authors used 1,2-diacetoxyethane as solvent for simple alcoholic acceptors (butyl, pentyl, hexyl, cyclohexyl, n-octyl, n-nonyl, n-decyl alcohols) and for phenol and 4-nitrophenol using almond β-glucosidase as catalyst [122].…”

Section: β-Glucosidasesmentioning

confidence: 99%

Glycosyl Hydrolases and Glycosyltransferases in the Synthesis of Oligosaccharides

Trincone¹,

Giordano

2006

COC

View full text Add to dashboard Cite

Glycobiology and related disciplines have received an enormous interest in recent years as they shed new light on the functional roles of carbohydrates in biological events leading to the understanding of mechanisms of important pathologies and to the development of new therapeutics. Although carbohydrate can be isolated from natural sources, the synthetic strategy plays its own role allowing access to larger quantities of structurally defined material and entry to analogs of naturally occurring structures. Nowadays, the bottleneck in this field is represented by some limitations of the potential of carbohydrate containing molecules because their complex structures make classical chemical synthesis very difficult.The synthesis of oligosaccharides have to face with three main snags: (i) reactivity of the leaving group on the monosaccharide acting as donor; (ii) regioselectivity towards a single hydroxyl group on the acceptor molecule; (iii) stereoselectivity in forming pure anomers of the new glycosidic product. The protecting-group manipulations that are needed for the stereocontrol of the products are demanding procedures thus yields and selectivity are lowered hindering the efficient production of oligosaccharides needed for biological testing.A particular benefit of the renewed interest for sugar chemistry has been the attention of scientific community to the biological methodologies in the production of oligosaccharides, an area which emerged in recent decades.In the carbohydrate field different enzymes were used for diverse purposes but enzymatic strategies for high-yield and stereospecific construction of glycosidic bonds are based on the action of two types of enzymes: glycosyl hydrolases (endo-and exo-glycosidases) and glycosyltransferases. Glycosyl hydrolases in the cells are responsible for the cleavage of glycosidic linkages; the exo-glycosidase are involved for glycan processing during in vivo glycoprotein synthesis. The glycosyltransferases are instead responsible in vivo for the synthesis of most cell-surface glycoconjugates.This review deals with the application of different types of glycosyl hydrolases. Elegant examples concerning the use of genetically modified representatives of glycosyl hydrolases (glycosynthases and thioglycoligases) will be also reported; some recent advances on the use of glycosyltransferases are also included.In compiling this review we were aware of the huge amount of excellent material published in the recent years on this topic, thus we will limit the covering of literature to the last decade. Attention will be devoted to the regioselectivity towards pyranosidic templates and to the yield of reactions. The molecular diversity obtained by the use of enzymes from different biological sources and the biological importance of the compounds synthesized will be focused as well.This review will put in evidence that glycosyl hydrolases and glycosyltransferases for the synthesis of the glycosidic linkages will play a relevant role in the next future as on the bench bio-catalysts ...

show abstract

Section: β-Glucosidasesmentioning

confidence: 99%

Glycosyl Hydrolases and Glycosyltransferases in the Synthesis of Oligosaccharides

Trincone¹,

Giordano

2006

COC

View full text Add to dashboard Cite

show abstract

“…On the other hand, the robust dextransucrase, a glucosyltransferase from Leuconostoc mesenteroides , displayed its optimal activity at 450 mM HQ, however, the product yield was low (0.44%) with respect to HQ . An approach to overcome the enzyme inactivation or inhibition caused by high HQ concentrations may be the use of an enzymatic reactor with a feeding strategy that avoids high acceptor concentrations .…”

Section: Resultsmentioning

confidence: 99%

Enzyme‐mediated transglycosylation of rutinose (6‐O‐α‐l‐rhamnosyl‐d‐glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697

Mazzaferro

Weiz

Braun

et al. 2018

Biotech and App Biochem

View full text Add to dashboard Cite

The structure of the carbohydrate moiety of a natural phenolic glycoside can have a significant effect on the molecular interactions and physicochemical and pharmacokinetic properties of the entire compound, which may include anti-inflammatory and anticancer activities. The enzyme 6-O-α-rhamnosyl-β-glucosidase (EC 3.2.1.168) has the capacity to transfer the rutinosyl moiety (6-O-α-L-rhamnopyranosylβ-D-glucopyranose) from 7-O-rutinosylated flavonoids to hydroxylated organic compounds. This transglycosylation reaction was optimized using hydroquinone (HQ) and hesperidin as rutinose acceptor and donor, respectively. Since HQ undergoes oxidation in a neutral to alkaline aqueous environment, the transglycosylation process was carried out at pH values ࣘ6.0. The structure of 4-hydroxyphenyl-β-rutinoside was confirmed by NMR, that is, a single glycosylated product with a free hydroxyl group was formed. The highest yield of 4-hydroxyphenyl-β-rutinoside (38%, regarding hesperidin) was achieved in a 2-h process at pH 5.0 and 30 • C, with 36 mM OH-acceptor and 5% (v/v) cosolvent. Under the same conditions, the enzyme synthesized glycoconjugates of various phenolic compounds (phloroglucinol, resorcinol, pyrogallol, catechol), with yields between 12% and 28% and an apparent direct linear relationship between the yield and the pK a value of the aglycon. This work is a contribution to the development of convenient and sustainable processes for the glycosylation of small phenolic compounds. C 2018 International

show abstract

“…The yield of alkyl β-D-glucoside is controlled by the thermodynamic equilibrium and the biocatalyst activity [16]. To verify the equilibrium yield of alkyl β-D-glucoside, both the hydrolysis and reverse-hydrolysis of propyl, hexyl, and octyl glucosides were performed (Fig.…”

Section: Equilibrium Between Glucoside Hydrolysis and Reverse Hydrolysismentioning

confidence: 99%

“…It is especially difficult to synthesize decyl β-D-glucoside containing a highly hydrophobic chain enzymatically using a general glucosidase. The reported yield of decyl glucoside was 0.8% even after 14 d of reaction by the reverse-hydrolysis pathway [16].…”

mentioning

confidence: 99%

“…Thereafter, more reports on the synthesis of alkyl β-glucosides have been published. Among them, hexyl [10][11][12][13][14][15][16][17][18][19][20] and octyl [12][13][14][15][16][17][18][19][20][21][22][23][24] β-D-glucosides were more extensively studied by comparison with the other glucosides containing long alkyl chains. However, the equilibrium constants and Gibbs free energies of glucosides with various alkyl chain lengths have never been reported or compared systematically in terms of thermodynamics.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Significantly Improved Equilibrium Yield of Long-Chain Alkyl Glucosides via Reverse Hydrolysis in a Water-Poor System Using Cross-Linked Almond Meal as a Cheap and Robust Biocatalyst

Wang¹,

Yu²,

Zhao³

et al. 2012

Chinese Journal of Catalysis

View full text Add to dashboard Cite

Novel reaction systems for the synthesis of O-glucosides by enzymatic reverse hydrolysis

Cited by 14 publications

References 19 publications

Glycosyl Hydrolases and Glycosyltransferases in the Synthesis of Oligosaccharides

Glycosyl Hydrolases and Glycosyltransferases in the Synthesis of Oligosaccharides

Enzyme‐mediated transglycosylation of rutinose (6‐O‐α‐l‐rhamnosyl‐d‐glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697

Significantly Improved Equilibrium Yield of Long-Chain Alkyl Glucosides via Reverse Hydrolysis in a Water-Poor System Using Cross-Linked Almond Meal as a Cheap and Robust Biocatalyst

Contact Info

Product

Resources

About