A Sustainable One-Pot, Two-Enzyme Synthesis of Naturally Occurring Arylalkyl Glucosides
Jazyk angličtina Země Německo Médium print-electronic
Typ dokumentu časopisecké články
PubMed
28186391
DOI
10.1002/cssc.201700136
Knihovny.cz E-zdroje
- Klíčová slova
- enzyme catalysis, glycosylation, green chemistry, natural products, synthetic methods,
- MeSH
- alkoholy chemie MeSH
- Aspergillus niger enzymologie MeSH
- biokatalýza MeSH
- glukosidy chemická syntéza MeSH
- glykosidhydrolasy metabolismus MeSH
- glykosylace MeSH
- rutin chemie MeSH
- technologie zelené chemie MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- alkoholy MeSH
- alpha-L-rhamnosidase MeSH Prohlížeč
- glukosidy MeSH
- glykosidhydrolasy 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.
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