Highly Regioselective and Efficient Biosynthesis of Polydatin by an Engineered UGTBL1-AtSuSy Cascade Reaction was written by Chen, Tianyi;Chen, Ziyi;Wang, Nan;Chu, Jianlin;Fan, Bo;Cheng, Cheng;Qin, Song;He, Bingfang. And the article was included in Journal of Agricultural and Food Chemistry in 2021.Synthetic Route of C20H22O8 The following contents are mentioned in the article:
Polydatin, resveratrol-3-O-β-glucoside, possesses various biol. activities. However, the regioselective glucosylation of resveratrol by UDP-glycosyltransferases (UGTs) constitutes a persistent problem. Semi-rational design and iterative combinatorial mutagenesis were carried out to screen the mutants of UGTBL1 and the high specificity with the glycosylation of the 3-OH group of resveratrol was explored. The triple mutant I62G/M112D/K143G exhibited near-perfect control of polydatin synthesis (regioselectivity ~99%), and the ratio of polydatin to resveratrol-4′-O-β-glucoside was finally enhanced by 786-fold. Mol. docking revealed that the mutant could form three H-bonds between 3-, 5-, and 4′-OH groups of resveratrol and the residues around the active center, resulting in the oriented-binding of resveratrol. Furthermore, UGTBL1 mutant coupling sucrose synthase AtSuSy can synthesize polydatin at an unprecedented high titer of 10.33 g/L, together with efficient UDPG regeneration (RCmax = 54). This study provides an efficient approach for the regioselective biosynthesis of polydatin. This study involved multiple reactions and reactants, such as (2S,3R,4S,5S,6R)-2-(3-Hydroxy-5-((E)-4-hydroxystyryl)phenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 27208-80-6Synthetic Route of C20H22O8).
(2S,3R,4S,5S,6R)-2-(3-Hydroxy-5-((E)-4-hydroxystyryl)phenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 27208-80-6) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.Synthetic Route of C20H22O8
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts