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Literature summary extracted from

  • Mazzaferro, L.S.; Weiz, G.; Braun, L.; Kotik, M.; Pelantova, H.; Kren, V.; Breccia, J.D.
    Enzyme-mediated transglycosylation of rutinose (6-O-alpha-L-rhamnosyl-D-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697 (2019), Biotechnol. Appl. Biochem., 66, 53-59 .
    View publication on PubMed

Activating Compound

EC Number Activating Compound Comment Organism Structure
3.2.1.168 dimethylformamide cosolvent DMF improves the transglycosylation yields in concentrations of 2%-10% v/v, whereas at higher concentrations (>20% v/v DMF), it turns out to be deleterious for the process Acremonium sp. DSM 24697
3.2.1.168 DMSO cosolvent DMF improves the transglycosylation yields in concentrations of 2%-10% v/v, whereas at higher concentrations (>30% v/v DMSO), it turns out to be deleterious for the process Acremonium sp. DSM 24697

Application

EC Number Application Comment Organism
3.2.1.168 additional information rutinose-containing glycoconjugates are resistant to hydrolysis in human tissues because of the absence of rutinoside-attacking glycosidases such as rhamnosidases or alpha-L-rhamnosyl-beta-D-glucosidases. Thus, rutinose-capped HQ may offer an additional advantage over other hydroquinone (HQ)-containing glycoconjugates in that it may be less prone to enzymatic degradation than, for example, glucosylated HQ when applied to human skin. Moreover, rutinosides have potential applications as food additives and antiviral agents Acremonium sp. DSM 24697

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.2.1.168 additional information
-
 additional information reaction kinetics, rutinoside transferase Acremonium sp. DSM 24697

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.2.1.168 hesperidin + H2O Acremonium sp. DSM 24697
-
 hesperitin + rutinose
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.2.1.168 Acremonium sp. DSM 24697 A0A286JZ59
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
3.2.1.168 native enzyme from culture supernatant to homogeneity by hydrophobic interaction and anion exchange chromatography Acremonium sp. DSM 24697

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.2.1.168 2-phenylethanol + hesperidin
-
 Acremonium sp. DSM 24697 2-phenylethyl beta-D-rutinoside + hesperetin
-
 ?
3.2.1.168 catechol + hesperidin
-
 Acremonium sp. DSM 24697 2-hydroxyphenyl beta-D-rutinoside + hesperetin
-
 ?
3.2.1.168 geraniol + hesperidin
-
 Acremonium sp. DSM 24697 geranyl beta-D-rutinoside + hesperetin
-
 ?
3.2.1.168 hesperidin + H2O
-
 Acremonium sp. DSM 24697 hesperitin + rutinose
-
 ?
3.2.1.168 hesperidin + H2O 6-O-alpha-rhamnosyl-beta-glucosidase activity Acremonium sp. DSM 24697 hesperitin + rutinose
-
 ?
3.2.1.168 hydroquinone + hesperidin
-
 Acremonium sp. DSM 24697 4-hydroxyphenyl-beta-D-rutinoside + hesperetin
-
 ?
3.2.1.168 additional information diglycosidase enzyme mediates transglycosylation of rutinose (6-O-alpha-L-rhamnosyl-D-glucose) to phenolic compounds. The enzyme 6-O-alpha-rhamnosyl-beta-glucosidase has the capacity to transfer the rutinosyl moiety (6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranose) from 7-O-rutinosylated flavonoids to hydroxylated organic compounds. This transglycosylation reaction is optimized using hydroquinone (HQ) and hesperidin as rutinose acceptor and donor, respectively. Formation of 4-hydroxyphenyl-beta-rutinoside, NMR analysis. The highest yield of 4-hydroxyphenyl-beta-rutinoside (38%, regarding hesperidin) is achieved in a 2-h process at pH 5.0 and 30°C, with 36 mM OH-acceptor and 5% v/v cosolvent. Under the same conditions, the enzyme synthesized glycoconjugates of various phenolic compounds (phloroglucinol, resorcinol, pyrogallol, catechol), with yields between 12% and 28% and an apparent direct linear relationship between the yield and the pKa value of the aglycon. Use of organic cosolvents (e.g. DMF or DMSO) as a means to increase the availability of the substrate in the reaction medium. The enzyme also efficiently rutinosylates specific hydroxy-acceptor compounds such as 2-phenylethanol, geraniol, and nerol without displaying significant hydrolysis activities Acremonium sp. DSM 24697 ?
-
 ?
3.2.1.168 nerol + hesperidin
-
 Acremonium sp. DSM 24697 neryl beta-D-rutinoside + hesperetin
-
 ?
3.2.1.168 phloroglucinol + hesperidin
-
 Acremonium sp. DSM 24697 3,5-dihydroxyphenyl beta-D-rutinoside + hesperetin
-
 ?
3.2.1.168 pyrogallol + hesperidin
-
 Acremonium sp. DSM 24697 2,3-dihydroxyphenyl beta-D-rutinoside + hesperetin
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.2.1.168 6-O-alpha-rhamnosyl-beta-glucosidase
-
 Acremonium sp. DSM 24697
3.2.1.168 alphaRbetaG
-
 Acremonium sp. DSM 24697
3.2.1.168 rutinoside transferase
-
 Acremonium sp. DSM 24697

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.2.1.168 30
-
 rutinoside transferase Acremonium sp. DSM 24697
3.2.1.168 60
-
 6-O-alpha-rhamnosyl-beta-glucosidase Acremonium sp. DSM 24697

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.2.1.168 5
-
 6-O-alpha-rhamnosyl-beta-glucosidase and rutinoside transferase Acremonium sp. DSM 24697

Expression

EC Number Organism Comment Expression
3.2.1.168 Acremonium sp. DSM 24697 hesperidin acts as both a carbon source and an inducer of the alpha-rhamnosyl-beta-glucosidase up