A Sustainable One-Pot, Two-Enzyme Synthesis of Naturally Occurring Arylalkyl Glucosides
Language English Country Germany Media print-electronic
Document type Journal Article
- Keywords
- enzyme catalysis, glycosylation, green chemistry, natural products, synthetic methods,
- MeSH
- Alcohols chemistry MeSH
- Aspergillus niger enzymology MeSH
- Biocatalysis MeSH
- Glucosides chemical synthesis MeSH
- Glycoside Hydrolases metabolism MeSH
- Glycosylation MeSH
- Rutin chemistry MeSH
- Green Chemistry Technology MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Alcohols MeSH
- alpha-L-rhamnosidase MeSH Browser
- Glucosides MeSH
- Glycoside Hydrolases MeSH
- Rutin MeSH
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.
References provided by Crossref.org
Flavonoids as Aglycones in Retaining Glycosidase-Catalyzed Reactions: Prospects for Green Chemistry
"Sweet Flavonoids": Glycosidase-Catalyzed Modifications
