Two Trifunctional Leloir Glycosyltransferases as Biocatalysts for Natural Products Glycodiversification

Pandey, Ramesh Prasad; Bashyal, Puspalata; Parajuli, Prakash; Yamaguchi, Tokutaro; Sohng, Jae Kyung

doi:10.1021/acs.orglett.9b03040

Cited by 20 publications

(24 citation statements)

References 39 publications

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“…Differentiation between 4′‐ O ‐ and 5‐ O ‐glycosylation sites can be performed on the basis of the fragmentation of [M + H] + ions. Namely, the loss of sugar moiety from position 4′ occurs with similar efficiency to the loss of sugar moiety from position 7 3,39,40 . Therefore, it is definitely a less efficient process than the loss of sugar moiety from position 5.…”

Section: Resultsmentioning

confidence: 99%

Electrospray ionisation mass spectrometric behaviour of flavonoid 5‐O‐glucosides and their positional isomers detected in the extracts from the bark of Prunus cerasus L. and Prunus avium L.

Beszterda

Frański

2020

Phytochemical Analysis

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Introduction Literature data concerning the electrospray ionisation mass spectrometry (ESI‐MS) behaviour of flavonoid 5‐O‐glycosides are poor and sometimes disputable. Therefore, we decided to analyse the compounds of this kind present in the bark of Prunus cerasus and Prunus avium by using high‐performance liquid chromatography HPLC/ESI‐MS. Objective The aim of this study is to obtain the comprehensive information about the ESI‐MS(+/−) behaviour of flavonoid 5‐O‐glucosides, to compare their behaviour with that of their positional isomers, to confirm that the known susceptibility of flavonoid 5‐O‐glucosides to hydrolysis may be successfully used for their identification. Method The bark from Prunus trees was extracted with pure methanol or, in order to perform hydrolysis and extraction simultaneously, with 5% methanolic solution of hydrochloric acid. The HPLC‐ESI‐MS analyses were performed using a Waters model 2690 HPLC pump and Waters/Micromass ZQ2000 mass spectrometer. Results Flavonoid 5‐O‐glycosides were completely hydrolysed under the acid conditions used, in contrast to their positional isomers. In positive ion mode, at low cone voltage, flavonoid 5‐O‐glycosides yield abundant Y0+ aglycone ions, in contrast to their positional isomers. In the negative ion mode, flavonoid 5‐O‐glycosides do not yield [Y0 − H]−· fragment ions, in contrast to their positional isomers. When aglycone contains only two hydroxyl groups, the flavonoid 5‐O‐glycosides can be detected in negative ion mode, whereas their positional isomers do not yield [M − H]− ions. Conclusion It has been demonstrated that the susceptibility to hydrolysis of the analysed compounds, the abundances of respective fragment ions formed, and their ESI(−) response allow unambiguous identification of flavonoid 5‐O‐glycosides and their differentiation from their positional isomers.

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Section: Resultsmentioning

confidence: 99%

Electrospray ionisation mass spectrometric behaviour of flavonoid 5‐O‐glucosides and their positional isomers detected in the extracts from the bark of Prunus cerasus L. and Prunus avium L.

Beszterda

Frański

2020

Phytochemical Analysis

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“…On the other hand, the discovery of the potential pharmacological activity of these three chalcone glucosides becomes possible. Compared with GTs from plants, microbial GTs generally exhibit remarkable substrate universality [13,14]. Our previous study has proved that BsGT1 from B. subtilis ATCC 6633 had excellent glycosylation ability toward curcumin and analogs [9].…”

Section: Discussionmentioning

confidence: 99%

Biosynthesis of Three Chalcone β-D-glucosides by Glycosyltransferase from Bacillus subtilis ATCC 6633

Fei¹,

Shao²,

Wang³

et al. 2021

Kor. J. Microbiol. Biotechnol

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“…While there have been numerous studies on glycosylation, particularly flavonoids O -glucosides and C -glucosides, very few studies on N -glucosides have been reported [ 16 ]. Recently, our group has explored the N -glycosyltransferase activity of YdhE [ 17 ], which has been observed to have the potential to serve as an important platform for the biosynthesis of bioactive N -glycosylated compounds ( Figure 1 ). However, in vitro enzymatic catalysis requires equimolar amounts of expensive uridine diphosphate (UDP)-sugar which is not feasible economically on a large-scale production.…”

Section: Introductionmentioning

confidence: 99%

N-Glucosylation in Corynebacterium glutamicum with YdhE from Bacillus lichenformis

2022

Self Cite

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Corynebacterium glutamicum is traditionally known as a food-grade microorganism due to its high ability to produce amino acids and its endotoxin-free recombinant protein expression factory. In recent years, studies to improve the activities of useful therapeutics and pharmaceutical compounds have led to the engineering of the therapeutically advantageous C. glutamicum cell factory system. One of the well-studied ways to improve the activities of useful compounds is glucosylation with glycosyltransferases. In this study, we successfully and efficiently glycosylated therapeutic butyl-4-aminobenzoate and other N-linked compounds in C. glutamicum using a promiscuous YdhE, which is a glycosyltransferase from Bacillus lichenformis. For efficient glucosylation, components, such as promoter, codons sequence, expression temperatures, and substrate and glucose concentrations were optimized. With glucose as the sole carbon source, we achieved a conversion rate of almost 96% of the glycosylated products in the culture medium. The glycosylated product of high concentration was successfully purified by a simple purification method, and subjected to further analysis. This is a report of the in vivo cultivation and glucosylation of N-linked compounds in C. glutamicum.

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Two Trifunctional Leloir Glycosyltransferases as Biocatalysts for Natural Products Glycodiversification

Cited by 20 publications

References 39 publications

Electrospray ionisation mass spectrometric behaviour of flavonoid 5‐O‐glucosides and their positional isomers detected in the extracts from the bark of Prunus cerasus L. and Prunus avium L.

Electrospray ionisation mass spectrometric behaviour of flavonoid 5‐O‐glucosides and their positional isomers detected in the extracts from the bark of Prunus cerasus L. and Prunus avium L.

Biosynthesis of Three Chalcone β-D-glucosides by Glycosyltransferase from Bacillus subtilis ATCC 6633

N-Glucosylation in Corynebacterium glutamicum with YdhE from Bacillus lichenformis

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