Glycosidase-Catalyzed Synthesis of Glycosyl Esters and Phenolic Glycosides of Aromatic Acids

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F19%3A00506191" target="_blank" >RIV/61388963:_____/19:00506191 - isvavai.cz</a>
Alternative codes found
RIV/61388971:_____/19:00506191
Result on the web
<a href="https://onlinelibrary.wiley.com/doi/full/10.1002/adsc.201900259" target="_blank" >https://onlinelibrary.wiley.com/doi/full/10.1002/adsc.201900259</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/adsc.201900259" target="_blank" >10.1002/adsc.201900259</a>

Result language
angličtina
Original language name
Glycosidase-Catalyzed Synthesis of Glycosyl Esters and Phenolic Glycosides of Aromatic Acids
Original language description
Phenolic glycosides occur naturally in many plants and as such are often present in the human diet. Their isolation from natural sources is usually laborious due to their presence in complex matrices. Their chemical and enzymatic syntheses have been found complex, time-consuming, and costly, yielding only small amounts of glycosylated products. In quest of a convenient biocatalytic route to structurally complex phenolic glycosides, we discovered that the rutinosidase from Aspergillus niger not only efficiently converts hydroxylated aromatic acids (e. g. coumaric and ferulic acids) into the respective phenolic rutinosides, but surprisingly also catalyzes the formation of the respective glycosyl esters. We report here the results of a systematic study presenting the unique synthesis of naturally occurring glycosyl esters and phenolic glycosides accomplished by glycosidase catalysis. A panel of aromatic acids was tested as glycosyl acceptors and the crucial structural features required for the formation of glycosyl esters were identified. In the light of the present structure-activity relationship study, a plausible reaction mechanism was proposed. All the products were fully structurally characterized by NMR and MS.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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