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- Name help_outline (2S)-hesperidin Identifier CHEBI:28775 (CAS: 520-26-3) help_outline Charge 0 Formula C28H34O15 InChIKeyhelp_outline QUQPHWDTPGMPEX-QJBIFVCTSA-N SMILEShelp_outline COc1ccc(cc1O)[C@@H]1CC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)cc2O1 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 H2O Identifier CHEBI:15377 (CAS: 7732-18-5) help_outline Charge 0 Formula H2O InChIKeyhelp_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILEShelp_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,485 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline rutinose Identifier CHEBI:27522 (CAS: 90-74-4) help_outline Charge 0 Formula C12H22O10 InChIKeyhelp_outline OVVGHDNPYGTYIT-BNXXONSGSA-N SMILEShelp_outline C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O 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 (2S)-hesperetin Identifier CHEBI:28230 (CAS: 520-33-2) help_outline Charge 0 Formula C16H14O6 InChIKeyhelp_outline AIONOLUJZLIMTK-AWEZNQCLSA-N SMILEShelp_outline COc1ccc(cc1O)[C@@H]1CC(=O)c2c(O)cc(O)cc2O1 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
Cross-references
| RHEA:28134 | RHEA:28135 | RHEA:28136 | RHEA:28137 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Extracellular monoenzyme deglycosylation system of 7-O-linked flavonoid beta-rutinosides and its disaccharide transglycosylation activity from Stilbella fimetaria.
Mazzaferro L., Pinuel L., Minig M., Breccia J.D.
We screened for microorganisms able to use flavonoids as a carbon source; and one isolate, nominated Stilbella fimetaria SES201, was found to possess a disaccharide-specific hydrolase. It was a cell-bound ectoenzyme that was released to the medium during conidiogenesis. The enzyme was shown to cle ... >> More
We screened for microorganisms able to use flavonoids as a carbon source; and one isolate, nominated Stilbella fimetaria SES201, was found to possess a disaccharide-specific hydrolase. It was a cell-bound ectoenzyme that was released to the medium during conidiogenesis. The enzyme was shown to cleave the flavonoid hesperidin (hesperetin 7-O-alpha-rhamnopyranosyl-beta-glucopyranoside) into rutinose (alpha-rhamnopyranosyl-beta-glucopyranose) and hesperetin. Since only intracellular traces of monoglycosidase activities (beta-glucosidase, alpha-rhamnosidase) were produced, the disaccharidase alpha-rhamnosyl-beta-glucosidase was the main system utilized by the microorganism for hesperidin hydrolysis. The enzyme was a glycoprotein with a molecular weight of 42224 Da and isoelectric point of 5.7. Even when maximum activity was found at 70 degrees C, it was active at temperatures as low as 5 degrees C, consistent with the psychrotolerant character of S. fimetaria. Substrate preference studies indicated that the enzyme exhibits high specificity toward 7-O-linked flavonoid beta-rutinosides. It did not act on flavonoid 3-O-beta-rutinoside and 7-O-beta-neohesperidosides, neither monoglycosylated substrates. In an aqueous medium, the alpha-rhamnosyl-beta-glucosidase was also able to transfer rutinose to other acceptors besides water, indicating its potential as biocatalyst for organic synthesis. The monoenzyme strategy of Acremonium sp. SES201 = DSM 24697, [corrected] as well as the enzyme substrate preference for 7-O-beta-flavonoid rutinosides, is unique characteristics among the microbial flavonoid deglycosylation systems reported. << Less