Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 3.2.1.168 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
Search for more literature for 3.2.1.168

Activating Compound

Activating Compound Comment Organism Structure
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
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

Application Comment Organism
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]

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

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Acremonium sp. DSM 24697 A0A286JZ59
-
-

Purification (Commentary)

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

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2-phenylethanol + hesperidin
-
 Acremonium sp. DSM 24697 2-phenylethyl beta-D-rutinoside + hesperetin
-
 ?
catechol + hesperidin
-
 Acremonium sp. DSM 24697 2-hydroxyphenyl beta-D-rutinoside + hesperetin
-
 ?
geraniol + hesperidin
-
 Acremonium sp. DSM 24697 geranyl beta-D-rutinoside + hesperetin
-
 ?
hesperidin + H2O
-
 Acremonium sp. DSM 24697 hesperitin + rutinose
-
 ?
hesperidin + H2O 6-O-alpha-rhamnosyl-beta-glucosidase activity Acremonium sp. DSM 24697 hesperitin + rutinose
-
 ?
hydroquinone + hesperidin
-
 Acremonium sp. DSM 24697 4-hydroxyphenyl-beta-D-rutinoside + hesperetin
-
 ?
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 ?
-
 ?
nerol + hesperidin
-
 Acremonium sp. DSM 24697 neryl beta-D-rutinoside + hesperetin
-
 ?
phloroglucinol + hesperidin
-
 Acremonium sp. DSM 24697 3,5-dihydroxyphenyl beta-D-rutinoside + hesperetin
-
 ?
pyrogallol + hesperidin
-
 Acremonium sp. DSM 24697 2,3-dihydroxyphenyl beta-D-rutinoside + hesperetin
-
 ?

Synonyms

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

Temperature Optimum [°C]

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

pH Optimum

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

Expression

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