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- Name help_outline mogroside V Identifier CHEBI:229959 Charge 0 Formula C60H102O29 InChIKeyhelp_outline GHBNZZJYBXQAHG-KUVSNLSMSA-N SMILEShelp_outline O[C@H]1[C@@]2([C@]([C@]3([C@@]([C@](CC3)([C@@H](CC[C@@H](O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O[C@@H]5O[C@@H]([C@@H](O)[C@H](O)[C@H]5O)CO)CO[C@@H]6O[C@@H]([C@@H](O)[C@H](O)[C@H]6O)CO)C(O)(C)C)C)[H])(C1)C)C)(CC=C7[C@]2(CC[C@H](O[C@@H]8O[C@@H]([C@@H](O)[C@H](O)[C@H]8O)CO[C@@H]9O[C@@H]([C@@H](O)[C@H](O)[C@H]9O)CO)C7(C)C)[H])[H])C 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-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 256 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline mogroside VI Identifier CHEBI:232052 Charge 0 Formula C66H112O34 InChIKeyhelp_outline LTDANPHZAHSOBN-ISABJOOBSA-N SMILEShelp_outline O[C@H]1[C@@]2([C@]([C@]3([C@@]([C@](CC3)([C@@H](CC[C@@H](O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O[C@@H]5O[C@@H]([C@@H](O)[C@H](O)[C@H]5O)CO)CO[C@@H]6O[C@@H]([C@@H](O)[C@H](O)[C@H]6O)CO)C(O)(C)C)C)[H])(C1)C)C)(CC=C7[C@]2(CC[C@H](O[C@@H]8O[C@@H]([C@@H](O)[C@H](O)[C@H]8O[C@@H]9O[C@@H]([C@@H](O)[C@H](O)[C@H]9O)CO)CO[C@@H]%10O[C@@H]([C@@H](O)[C@H](O)[C@H]%10O)CO)C7(C)C)[H])[H])C 2D coordinates Mol file for the small molecule Search links Involved in 1 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 611 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 9,717 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:81943 | RHEA:81944 | RHEA:81945 | RHEA:81946 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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The biosynthetic pathway of the nonsugar, high-intensity sweetener mogroside V from Siraitia grosvenorii.
Itkin M., Davidovich-Rikanati R., Cohen S., Portnoy V., Doron-Faigenboim A., Oren E., Freilich S., Tzuri G., Baranes N., Shen S., Petreikov M., Sertchook R., Ben-Dor S., Gottlieb H., Hernandez A., Nelson D.R., Paris H.S., Tadmor Y., Burger Y., Lewinsohn E., Katzir N., Schaffer A.
The consumption of sweeteners, natural as well as synthetic sugars, is implicated in an array of modern-day health problems. Therefore, natural nonsugar sweeteners are of increasing interest. We identify here the biosynthetic pathway of the sweet triterpenoid glycoside mogroside V, which has a swe ... >> More
The consumption of sweeteners, natural as well as synthetic sugars, is implicated in an array of modern-day health problems. Therefore, natural nonsugar sweeteners are of increasing interest. We identify here the biosynthetic pathway of the sweet triterpenoid glycoside mogroside V, which has a sweetening strength of 250 times that of sucrose and is derived from mature fruit of luo-han-guo (Siraitia grosvenorii, monk fruit). A whole-genome sequencing of Siraitia, leading to a preliminary draft of the genome, was combined with an extensive transcriptomic analysis of developing fruit. A functional expression survey of nearly 200 candidate genes identified the members of the five enzyme families responsible for the synthesis of mogroside V: squalene epoxidases, triterpenoid synthases, epoxide hydrolases, cytochrome P450s, and UDP-glucosyltransferases. Protein modeling and docking studies corroborated the experimentally proven functional enzyme activities and indicated the order of the metabolic steps in the pathway. A comparison of the genomic organization and expression patterns of these Siraitia genes with the orthologs of other Cucurbitaceae implicates a strikingly coordinated expression of the pathway in the evolution of this species-specific and valuable metabolic pathway. The genomic organization of the pathway genes, syntenously preserved among the Cucurbitaceae, indicates, on the other hand, that gene clustering cannot account for this novel secondary metabolic pathway. << Less
Proc. Natl. Acad. Sci. U.S.A. 113:E7619-E7628(2016) [PubMed] [EuropePMC]
This publication is cited by 22 other entries.