Back to Search
Start Over
Using Amylosucrase for the Controlled Synthesis of Novel Isoquercitrin Glycosides with Different Glycosidic Linkages
- Source :
- Journal of Agricultural and Food Chemistry. 68:13798-13805
- Publication Year :
- 2020
- Publisher :
- American Chemical Society (ACS), 2020.
-
Abstract
- Many attempts have been made to obtain natural products with certain glycosidic linkages for improvement of their chemo-physical characteristics. Amylosucrase from Deinococcus geothermalis (DGAS; EC.4.2.1.4) is able to transglycosylate natural products. A model compound, isoquercitrin (IQ; quercetin-3-O-glucoside), was employed for producing new IQ glucosides (IQ-Gs). Treatment of IQ with DGAS produced monoglucoside (IQ-G1'), diglucosides (IQ-G2' and IQ-G2″), and triglucoside (IQ-G3). Structural analysis by mass and nuclear magnetic resonance spectrometry revealed that three of the four IQ-Gs were unreported new compounds possessing α-1,2-, α-1,4-, and/or α-1,6-glucosidic linkages at the 3-O-glucosyl moiety of IQ. IQ-G2' and IQ-G3 were dominantly produced at pH 5.0 and 7.2 and 1500 and 100 mM sucrose, respectively (yields of total IQ-Gs: 50-97%). Kinetic studies indicated that the production rate was dependent on buffer/pH and sucrose concentration. The diverse transglycosylations were verified with a molecular docking simulation. This study sheds light on methods for simple glycodiversification of natural products using DGAS, which can synthesize diversely branched glycosides by modulating reaction conditions.
- Subjects :
- 0106 biological sciences
Glycosylation
Sucrose
Stereochemistry
01 natural sciences
Amylosucrase
chemistry.chemical_compound
Bacterial Proteins
Moiety
Glycosides
Reaction conditions
chemistry.chemical_classification
biology
Chemistry
010401 analytical chemistry
Regioselectivity
Glycoside
Glycosidic bond
General Chemistry
biology.organism_classification
0104 chemical sciences
Molecular Docking Simulation
Kinetics
Glucosyltransferases
biology.protein
Quercetin
Deinococcus
General Agricultural and Biological Sciences
Deinococcus geothermalis
010606 plant biology & botany
Subjects
Details
- ISSN :
- 15205118 and 00218561
- Volume :
- 68
- Database :
- OpenAIRE
- Journal :
- Journal of Agricultural and Food Chemistry
- Accession number :
- edsair.doi.dedup.....2708b56747b1ad95a10645342777a3f8