Reaction participants Show >> << Hide
- Name help_outline 3-O-{β-D-Xyl-(1→3)-[β-D-Gal-(1→2)]-β-D-GlcA}-quillaic acid 4-dehydro-6-deoxy-β-D-Glc ester Identifier CHEBI:234191 Charge -1 Formula C53H79O24 InChIKeyhelp_outline ILWPPZWOHMMEJZ-WVNFMIJOSA-M SMILEShelp_outline [H]C12C3=CCC4([H])C5(C)CCC(OC6OC(C(=O)[O-])C(O)C(OC7OCC(O)C(O)C7O)C6OC8OC(CO)C(O)C(O)C8O)C(C=O)(C)C5([H])CCC4(C)C3(C)CC(O)C2(C(=O)OC9OC(C(=O)C(O)C9O)C)CCC(C)(C)C1 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 NADPH Identifier CHEBI:57783 (Beilstein: 10411862) help_outline Charge -4 Formula C21H26N7O17P3 InChIKeyhelp_outline ACFIXJIJDZMPPO-NNYOXOHSSA-J SMILEShelp_outline NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,365 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 10,232 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 3-O-{β-D-Xyl-(1→3)-[β-D-Gal-(1→2)]-β-D-GlcA}-quillaic acid β-D-Fuc ester Identifier CHEBI:234170 Charge -1 Formula C53H81O24 InChIKeyhelp_outline CUIIBCJGZMKLOJ-ZEUZCOCPSA-M SMILEShelp_outline [H]C12C3=CCC4([H])C5(C)CCC(OC6OC(C(=O)[O-])C(O)C(OC7OCC(O)C(O)C7O)C6OC8OC(CO)C(O)C(O)C8O)C(C=O)(C)C5([H])CCC4(C)C3(C)CC(O)C2(C(=O)OC9OC(C)C(O)C(O)C9O)CCC(C)(C)C1 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 NADP+ Identifier CHEBI:58349 Charge -3 Formula C21H25N7O17P3 InChIKeyhelp_outline XJLXINKUBYWONI-NNYOXOHSSA-K SMILEShelp_outline NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,372 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:85047 | RHEA:85048 | RHEA:85049 | RHEA:85050 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Related reactions help_outline
More general form(s) of this reaction
Publications
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Elucidation of the pathway for biosynthesis of saponin adjuvants from the soapbark tree.
Reed J., Orme A., El-Demerdash A., Owen C., Martin L.B.B., Misra R.C., Kikuchi S., Rejzek M., Martin A.C., Harkess A., Leebens-Mack J., Louveau T., Stephenson M.J., Osbourn A.
The Chilean soapbark tree (<i>Quillaja saponaria</i>) produces soap-like molecules called QS saponins that are important vaccine adjuvants. These highly valuable compounds are sourced by extraction from the bark, and their biosynthetic pathway is unknown. Here, we sequenced the <i>Q. saponaria</i> ... >> More
The Chilean soapbark tree (<i>Quillaja saponaria</i>) produces soap-like molecules called QS saponins that are important vaccine adjuvants. These highly valuable compounds are sourced by extraction from the bark, and their biosynthetic pathway is unknown. Here, we sequenced the <i>Q. saponaria</i> genome. Through genome mining and combinatorial expression in tobacco, we identified 16 pathway enzymes that together enable the production of advanced QS pathway intermediates that represent a bridgehead for adjuvant bioengineering. We further identified the enzymes needed to make QS-7, a saponin with excellent therapeutic properties and low toxicity that is present in low abundance in <i>Q. saponaria</i> bark extract. Our results enable the production of <i>Q. saponaria</i> vaccine adjuvants in tobacco and open the way for new routes to access and engineer natural and new-to-nature immunostimulants. << Less
Science 379:1252-1264(2023) [PubMed] [EuropePMC]
This publication is cited by 16 other entries.
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Unlocking saponin biosynthesis in soapwort.
Jo S., El-Demerdash A., Owen C., Srivastava V., Wu D., Kikuchi S., Reed J., Hodgson H., Harkess A., Shu S., Plott C., Jenkins J., Williams M., Boston L.-B., Lacchini E., Qu T., Goossens A., Grimwood J., Schmutz J., Leebens-Mack J., Osbourn A.
Soapwort (Saponaria officinalis) is a flowering plant from the Caryophyllaceae family with a long history of human use as a traditional source of soap. Its detergent properties are because of the production of polar compounds (saponins), of which the oleanane-based triterpenoid saponins, saponario ... >> More
Soapwort (Saponaria officinalis) is a flowering plant from the Caryophyllaceae family with a long history of human use as a traditional source of soap. Its detergent properties are because of the production of polar compounds (saponins), of which the oleanane-based triterpenoid saponins, saponariosides A and B, are the major components. Soapwort saponins have anticancer properties and are also of interest as endosomal escape enhancers for targeted tumor therapies. Intriguingly, these saponins share common structural features with the vaccine adjuvant QS-21 and, thus, represent a potential alternative supply of saponin adjuvant precursors. Here, we sequence the S. officinalis genome and, through genome mining and combinatorial expression, identify 14 enzymes that complete the biosynthetic pathway to saponarioside B. These enzymes include a noncanonical cytosolic GH1 (glycoside hydrolase family 1) transglycosidase required for the addition of D-quinovose. Our results open avenues for accessing and engineering natural and new-to-nature pharmaceuticals, drug delivery agents and potential immunostimulants. << Less
Nat. Chem. Biol. 21:215-226(2025) [PubMed] [EuropePMC]
This publication is cited by 11 other entries.