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Information on EC 2.4.1.363 - ginsenoside 20-O-glucosyltransferase for references in articles please use BRENDA:EC2.4.1.363
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IUBMB Comments The enzyme, characterized from the plant Panax ginseng, transfers a glucosyl moiety to the free C20(S)-OH group of dammarane derivative substrates, including protopanaxatriol, dammarenediol II, (20S)-ginsenoside Rh2, and (20S)-ginsenoside Rg3. It does not act on the 20R epimer of protopanaxadiol, or on ginsenosides that are glucosylated at the C-6 position, such as ginsenoside Rh1 or ginsenoside Rg2.
The expected taxonomic range for this enzyme is: Panax ginseng
Synonyms
UGT, UGT71A27, UGTPg1, UGTPg102, UGTPg103, uridine diphosphate glycosyltransferase,
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uridine diphosphate glycosyltransferase
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UGTPg1
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UDP-alpha-D-glucose + (20S)-protopanaxadiol = UDP + ginsenoside C-K
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UDP-alpha-D-glucose:(20S)-protopanaxadiol 20-O-glucosyltransferase (configuration-inverting)
The enzyme, characterized from the plant Panax ginseng, transfers a glucosyl moiety to the free C20(S)-OH group of dammarane derivative substrates, including protopanaxatriol, dammarenediol II, (20S)-ginsenoside Rh2, and (20S)-ginsenoside Rg3. It does not act on the 20R epimer of protopanaxadiol, or on ginsenosides that are glucosylated at the C-6 position, such as ginsenoside Rh1 or ginsenoside Rg2.
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UDP-alpha-D-glucose + (20S)-protopanaxadiol
UDP + ginsenoside C-K
UDP-alpha-D-glucose + (20S)-protopanaxatriol
UDP + ginsenoside F1
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the reaction is catalyzed by the enzyme isoform UGTPg1
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UDP-alpha-D-glucose + dammarenediol II
UDP + 20S-O-beta-(D-glucosyl)-dammarenediol II
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preferred substrate
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UDP-alpha-D-glucose + ginsenoside Rg3
UDP + ginsenoside Rd
UDP-alpha-D-glucose + ginsenoside Rh2
UDP + ginsenoside F2
additional information
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UDP-alpha-D-glucose + (20S)-protopanaxadiol
UDP + ginsenoside C-K
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UDP-alpha-D-glucose + (20S)-protopanaxadiol
UDP + ginsenoside C-K
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the reaction is catalyzed by the enzyme isoform UGTPg1
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UDP-alpha-D-glucose + ginsenoside Rg3
UDP + ginsenoside Rd
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UDP-alpha-D-glucose + ginsenoside Rg3
UDP + ginsenoside Rd
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the reaction is catalyzed by the enzyme isoform UGTPg1
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UDP-alpha-D-glucose + ginsenoside Rh2
UDP + ginsenoside F2
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UDP-alpha-D-glucose + ginsenoside Rh2
UDP + ginsenoside F2
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the reaction is catalyzed by the enzyme isoform UGTPg1
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additional information
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isoforms UGTPg102 and UGTPg103 have no detectable activity on (20S)-protopanaxatriol
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additional information
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the enzyme does not glucosylate (20R)-protopanaxadiol
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UDP-alpha-D-glucose + (20S)-protopanaxadiol
UDP + ginsenoside C-K
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0.104
(20S)-protopanaxadiol
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isoform UGTPg1, at pH 8.0 and 35°C
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17.9
(20S)-protopanaxadiol
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isoform UGTPg1, at pH 8.0 and 35°C
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170
(20S)-protopanaxadiol
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isoform UGTPg1, at pH 8.0 and 35°C
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brenda
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A40S
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the mutant of isoform UGTPg1 shows about wild type activity towards (20S)-protopanaxatriol
F85L
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the mutant of isoform UGTPg1 shows about wild type activity towards (20S)-protopanaxatriol
H144Y
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the mutant of isoform UGTPg1 is inactive towards (20S)-protopanaxatriol
L38F
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the mutant of isoform UGTPg1 shows about wild type activity towards (20S)-protopanaxatriol
Q388H
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the mutant of isoform UGTPg1 shows about wild type activity towards (20S)-protopanaxatriol
T134I
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the mutant of isoform UGTPg1 shows about wild type activity towards (20S)-protopanaxatriol
T142A
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the mutant of isoform UGTPg103 is inactive towards (20S)-protopanaxatriol
T142A/S186L
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the mutant of isoform UGTPg103 is inactive towards (20S)-protopanaxatriol
T142A/S186L/R338G
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the mutant of isoform UGTPg103 has activity to glycosylate the C6-OH of (20S)-protopanaxatriol
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expressed in Escherichia coli BL21(DE3) cells
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expressed in Saccharomyces cerevisiae strain AK1
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Yan, X.; Fan, Y.; Wei, W.; Wang, P.; Liu, Q.; Wei, Y.; Zhang, L.; Zhao, G.; Yue, J.; Zhou, Z.
Production of bioactive ginsenoside compound K in metabolically engineered yeast
Cell Res.
24
770-773
2014
Panax ginseng
brenda
Wei, W.; Wang, P.; Wei, Y.; Liu, Q.; Yang, C.; Zhao, G.; Yue, J.; Yan, X.; Zhou, Z.
Characterization of Panax ginseng UDP-glycosyltransferases catalyzing protopanaxatriol and biosyntheses of bioactive ginsenosides F1 and Rh1 in metabolically engineered yeasts
Mol. Plant
8
1412-1424
2015
Panax ginseng
brenda
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