Transglycosylation of L-ascorbic acid

Markosyan, A. A.; Abelyan, L. A.; Adamyan, M. O.; Akopyan, Zh. I.; Abelyan, V. A.

doi:10.1134/s0003683807010061

Cited by 5 publications

(3 citation statements)

References 15 publications

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“…Increasing production of AA-2G using highly soluble and low cost glycosyl donors such as maltose and maltodextrin was recently reported [2,3], but the yield was still low compared to other substrates. Maximum production of AA-2G has also been reported, using different substrates and enzymes in reactions lasting 24−48 h [4].…”

Section: Introductionmentioning

confidence: 92%

Improvement of 2-O-α-D-Glucopyranosyl-L-Ascorbic Acid Biosynthesis Using Ultrasonic Radiation

Eibaid¹,

Miao²,

Bashari³

2015

Trop. J. Pharm Res

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Section: Introductionmentioning

confidence: 92%

Improvement of 2-O-α-D-Glucopyranosyl-L-Ascorbic Acid Biosynthesis Using Ultrasonic Radiation

Eibaid¹,

Miao²,

Bashari³

2015

Trop. J. Pharm Res

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“…Although AA-2G can be produced by different enzymes [11,13,14], but studies have shown that cyclodextrin glucanotransferase (CGTase) is the most preferable either mostly in free [15], immobilized [16], recombinant [17], or in mutant state [18]. CGTase transfer glucose unit to C 2 in AA via transglycosylation from glycosyl donor, different substrates were used as glycosyl donor except glucose [15,17].…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of 2-O-α-D-glucopyranosyl-L-Ascorbic Acid from Maltose by Cyclodextrin Glucanotransferase from Bacillus sp. SK 13.002

Eibaid¹,

Bashari²,

Miao³

et al. 2014

JFNR

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In this work 2-O-α-D-glucopyranosyl-L-ascorbic acid (AA-2G) was synthesized by Cyclodextrin glucanotransferase (CGTase) from Bacillus sp. SK 13.002 with L-ascorbic acid (AA) as an acceptor and maltose as a glycosyl donor. AA-2G production was analyzed by HPLC and was confirmed by LC/MS results. The reaction parameters, such as pH (4.0-9.0), temperature (25-50°C), time (0-30 h), substrate ratios and enzyme concentration were optimized. The results showed that the optimum condition was pH 8.0 at 37°C for 24 h, 1:1 maltose to AA substrates mass ratio, and 200 U/mL of CGTase. Under these conditions, the production of AA-2G was 5.5 g/L, this result indicate that CGTase from Bacillus sp. SK 13.002 can effectively uses maltose as a glycosyl donor to produce AA-2G in high yield.

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“…Usually these transglycosidases catalyze the transfer of donor glycosides to the carbohydrate moiety of a natural product glycoside rather than to the aglycon, forming a multiple carbohydrate glycosylated natural product. Some transglycosidases can use simple small molecules as the acceptor substrates, such as hydroquinone and ascorbic acid 27 28 29 30 . By application of directed evolution methodologies, the activities of glycoside hydrolases or glycosynthases have been improved towards expanded sugar-donor or acceptor substrates 31 32 33 ; however, the transglycosylation activities on non-glycosylated natural-product acceptors still remain low.…”

mentioning

confidence: 99%

Engineering a Carbohydrate-processing Transglycosidase into Glycosyltransferase for Natural Product Glycodiversification

Liang

Zhang

Jia

et al. 2016

Sci Rep

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Glycodiversification broadens the scope of natural product-derived drug discovery. The acceptor substrate promiscuity of glucosyltransferase-D (GTF-D), a carbohydrate-processing enzyme from Streptococcus mutans, was expanded by protein engineering. Mutants in a site-saturation mutagenesis library were screened on the fluorescent substrate 4-methylumbelliferone to identify derivatives with improved transglycosylation efficiency. In comparison to the wild-type GTF-D enzyme, mutant M4 exhibited increased transglycosylation capabilities on flavonoid substrates including catechin, genistein, daidzein and silybin, using the glucosyl donor sucrose. This study demonstrated the feasibility of developing natural product glycosyltransferases by engineering transglycosidases that use donor substrates cheaper than NDP-sugars, and gave rise to a series of α-glucosylated natural products that are novel to the natural product reservoir. The solubility of the α-glucoside of genistein and the anti-oxidant capability of the α-glucoside of catechin were also studied.

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Transglycosylation of L-ascorbic acid

Cited by 5 publications

References 15 publications

Improvement of 2-O-α-D-Glucopyranosyl-L-Ascorbic Acid Biosynthesis Using Ultrasonic Radiation

Improvement of 2-O-α-D-Glucopyranosyl-L-Ascorbic Acid Biosynthesis Using Ultrasonic Radiation

Biosynthesis of 2-O-α-D-glucopyranosyl-L-Ascorbic Acid from Maltose by Cyclodextrin Glucanotransferase from Bacillus sp. SK 13.002

Engineering a Carbohydrate-processing Transglycosidase into Glycosyltransferase for Natural Product Glycodiversification

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