BIOMAT Database Logo BIOMAT Database Logo

A Sustainable One-Pot, Two-Enzyme Synthesis of Naturally Occurring Arylalkyl Glucosides. 2017

Ivan Bassanini, and Jana Krejzová, and Walter Panzeri, and Daniela Monti, and Vladimir Křen, and Sergio Riva
Istituto di Chimica del Riconoscimento Molecolare, Consiglio Nazionale delle Ricerche, Via Mario Bianco 9, Milano, 20131, Italy.

A sustainable, convenient, scalable, one-pot, two-enzyme method for the glucosylation of arylalkyl alcohols was developed. The reaction scheme is based on a transrutinosylation catalyzed by a rutinosidase from A. niger using the cheap commercially available natural flavonoid rutin as glycosyl donor, followed by selective "trimming" of the rutinoside unit catalyzed by a rhamnosidase from A. terreus. The process was validated with the syntheses of several natural bioactive glucosides, which could be isolated in up to 75 % yield without silica-gel chromatography.

UI MeSH Term Description Entries
D005960 Glucosides A GLYCOSIDE that is derived from GLUCOSE. Glucoside
D006026 Glycoside Hydrolases Any member of the class of enzymes that catalyze the cleavage of the glycosidic linkage of glycosides and the addition of water to the resulting molecules. Endoglycosidase,Exoglycosidase,Glycohydrolase,Glycosidase,Glycosidases,Glycoside Hydrolase,Endoglycosidases,Exoglycosidases,Glycohydrolases,Hydrolase, Glycoside,Hydrolases, Glycoside
D006031 Glycosylation The synthetic chemistry reaction or enzymatic reaction of adding carbohydrate or glycosyl groups. GLYCOSYLTRANSFERASES carry out the enzymatic glycosylation reactions. The spontaneous, non-enzymatic attachment of reducing sugars to free amino groups in proteins, lipids, or nucleic acids is called GLYCATION (see MAILLARD REACTION). Protein Glycosylation,Glycosylation, Protein
D000438 Alcohols Alkyl compounds containing a hydroxyl group. They are classified according to relation of the carbon atom: primary alcohols, R-CH2OH; secondary alcohols, R2-CHOH; tertiary alcohols, R3-COH. (From Grant & Hackh's Chemical Dictionary, 5th ed)
D001234 Aspergillus niger An imperfect fungus causing smut or black mold of several fruits and vegetables such as grapes, apricots, onions, and peanuts, and is a common contaminant of food. Aspergillus lacticoffeatus
D012431 Rutin A flavonol glycoside found in many plants, including BUCKWHEAT; TOBACCO; FORSYTHIA; HYDRANGEA; VIOLA, etc. It has been used therapeutically to decrease capillary fragility. 3-Rhamnosyl-Glucosyl Quercetin,Quercetin-3-Rutinoside,Rutoside,Quercetin 3 Rutinoside,Quercetin, 3-Rhamnosyl-Glucosyl
D055162 Biocatalysis The facilitation of biochemical reactions with the aid of naturally occurring catalysts such as ENZYMES.
D055772 Green Chemistry Technology Pollution prevention through the design of effective chemical products that have low or no toxicity and use of chemical processes that reduce or eliminate the use and generation of hazardous substances. Environmentally Friendly Chemical Techniques,Environmentally Friendly Chemical Technology,Environmentally Friendly Chemistry Technology,Green Chemical Techniques,Sustainable Chemistry Technology,Chemical Technique, Green,Chemical Techniques, Green,Chemistry Technologies, Green,Chemistry Technologies, Sustainable,Chemistry Technology, Green,Chemistry Technology, Sustainable,Green Chemical Technique,Green Chemistry Technologies,Sustainable Chemistry Technologies,Technique, Green Chemical,Techniques, Green Chemical,Technologies, Green Chemistry,Technologies, Sustainable Chemistry,Technology, Green Chemistry,Technology, Sustainable Chemistry

Related Publications

Ivan Bassanini, and Jana Krejzová, and Walter Panzeri, and Daniela Monti, and Vladimir Křen, and Sergio Riva
General and Stereocontrolled Approach to the Chemical Synthesis of Naturally Occurring Cyanogenic Glucosides.
April 2016, Journal of natural products,
Ivan Bassanini, and Jana Krejzová, and Walter Panzeri, and Daniela Monti, and Vladimir Křen, and Sergio Riva
One-pot synthesis of glutathione by a two-enzyme cascade using a thermophilic ATP regeneration system.
January 2017, Journal of biotechnology,
Ivan Bassanini, and Jana Krejzová, and Walter Panzeri, and Daniela Monti, and Vladimir Křen, and Sergio Riva
One-pot three-enzyme synthesis of UDP-GlcNAc derivatives.
October 2011, Chemical communications (Cambridge, England),
Ivan Bassanini, and Jana Krejzová, and Walter Panzeri, and Daniela Monti, and Vladimir Křen, and Sergio Riva
One-pot four-enzyme synthesis of thymidinediphosphate-l-rhamnose.
November 2016, Chemical communications (Cambridge, England),
Ivan Bassanini, and Jana Krejzová, and Walter Panzeri, and Daniela Monti, and Vladimir Křen, and Sergio Riva
One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines.
July 2012, Organic letters,
Ivan Bassanini, and Jana Krejzová, and Walter Panzeri, and Daniela Monti, and Vladimir Křen, and Sergio Riva
Total synthesis of two naturally occurring bicyclo[3.2.1]octanoid neolignans.
July 2002, The Journal of organic chemistry,
Ivan Bassanini, and Jana Krejzová, and Walter Panzeri, and Daniela Monti, and Vladimir Křen, and Sergio Riva
Synthesis of naturally occurring phosphonolipids.
June 1972, The Biochemical journal,
Ivan Bassanini, and Jana Krejzová, and Walter Panzeri, and Daniela Monti, and Vladimir Křen, and Sergio Riva
Synthesis of naturally occurring polyynes.
February 2006, Angewandte Chemie (International ed. in English),
Ivan Bassanini, and Jana Krejzová, and Walter Panzeri, and Daniela Monti, and Vladimir Křen, and Sergio Riva
One-pot multicomponent synthesis of two novel thiolactone scaffolds.
August 2010, Molecular diversity,
Ivan Bassanini, and Jana Krejzová, and Walter Panzeri, and Daniela Monti, and Vladimir Křen, and Sergio Riva
[Mustard oil glucosides as genuine mother substances of naturally occurring antithyroid materials].
January 1956, Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft,
Copied contents to your clipboard!