Reaction participants Show >> << Hide
- Name help_outline rebaudioside E Identifier CHEBI:145018 (CAS: 63279-14-1) help_outline Charge 0 Formula C44H70O23 InChIKeyhelp_outline RLLCWNUIHGPAJY-SFUUMPFESA-N SMILEShelp_outline O([C@@H]1O[C@@H]([C@@H](O)[C@@H]([C@H]1O[C@@H]2O[C@@H]([C@@H](O)[C@@H]([C@H]2O)O)CO)O)CO)C([C@]3([C@@]4([C@]([C@]5([C@]6(C[C@@](CC5)(C(C6)=C)O[C@H]7[C@H](O[C@@H]8O[C@@H]([C@@H](O)[C@@H]([C@H]8O)O)CO)[C@H]([C@H](O)[C@H](O7)CO)O)CC4)[H])(CCC3)C)[H])C)=O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline UDP-α-D-glucose Identifier CHEBI:58885 (Beilstein: 3827329) help_outline Charge -2 Formula C15H22N2O17P2 InChIKeyhelp_outline HSCJRCZFDFQWRP-JZMIEXBBSA-L SMILEShelp_outline OC[C@H]1O[C@H](OP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)n2ccc(=O)[nH]c2=O)[C@H](O)[C@@H](O)[C@@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 258 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline rebaudioside D Identifier CHEBI:145022 (CAS: 63279-13-0) help_outline Charge 0 Formula C50H80O28 InChIKeyhelp_outline RPYRMTHVSUWHSV-CUZJHZIBSA-N SMILEShelp_outline [C@]123[C@]([C@]4([C@@]([C@](CCC4)(C)C(O[C@@H]5O[C@@H]([C@@H](O)[C@@H]([C@H]5O[C@@H]6O[C@@H]([C@@H](O)[C@@H]([C@H]6O)O)CO)O)CO)=O)(CC1)[H])C)(CC[C@@](C2)(O[C@H]7[C@H](O[C@@H]8O[C@@H]([C@@H](O)[C@@H]([C@H]8O)O)CO)[C@H]([C@H](O)[C@H](O7)CO)O[C@@H]9O[C@@H]([C@@H](O)[C@@H]([C@H]9O)O)CO)C(C3)=C)[H] 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline UDP Identifier CHEBI:58223 Charge -3 Formula C9H11N2O12P2 InChIKeyhelp_outline XCCTYIAWTASOJW-XVFCMESISA-K SMILEShelp_outline O[C@@H]1[C@@H](COP([O-])(=O)OP([O-])([O-])=O)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O 2D coordinates Mol file for the small molecule Search links Involved in 637 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,932 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:61772 | RHEA:61773 | RHEA:61774 | RHEA:61775 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Hydrophobic recognition allows the glycosyltransferase UGT76G1 to catalyze its substrate in two orientations.
Yang T., Zhang J., Ke D., Yang W., Tang M., Jiang J., Cheng G., Li J., Cheng W., Wei Y., Li Q., Naismith J.H., Zhu X.
Diets high in sugar are recognized as a serious health problem, and there is a drive to reduce their consumption. Steviol glycosides are natural zero-calorie sweeteners, but the most desirable ones are biosynthesized with low yields. UGT76G1 catalyzes the β (1-3) addition of glucose to steviol gly ... >> More
Diets high in sugar are recognized as a serious health problem, and there is a drive to reduce their consumption. Steviol glycosides are natural zero-calorie sweeteners, but the most desirable ones are biosynthesized with low yields. UGT76G1 catalyzes the β (1-3) addition of glucose to steviol glycosides, which gives them the preferred taste. UGT76G1 is able to transfer glucose to multiple steviol substrates yet remains highly specific in the glycosidic linkage it creates. Here, we report multiple complex structures of the enzyme combined with biochemical data, which reveal that the enzyme utilizes hydrophobic interactions for substrate recognition. The lack of a strict three-dimensional recognition arrangement, typical of hydrogen bonds, permits two different orientations for β (1-3) sugar addition. The use of hydrophobic recognition is unusual in a regio- and stereo-specific catalysis. Harnessing such non-specific hydrophobic interactions could have wide applications in the synthesis of complex glycoconjugates. << Less
Nat. Commun. 10:3214-3214(2019) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.