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Literature summary extracted from

  • Verdoucq, L.; Czjzek, M.; Moriniere, J.; Bevan, D.R.; Esen, A.
    Mutational and structural analysis of aglycone specificity in maize and sorghum beta-glucosidases (2003), J. Biol. Chem., 278, 25055-25062.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
3.2.1.21 expressed in Escherichia coli as a His-tagged fusion protein Sorghum bicolor
3.2.1.21 expressed in Escherichia coli as a His-tagged fusion protein Zea mays

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
3.2.1.21 crystal structure of mutant E191D,F198V is determined at 1.9 A resolution in complex with DIMBOA-glucoside Zea mays

Protein Variants

EC Number Protein Variants Comment Organism
3.2.1.21 A375P Km (2-nitrophenyl beta-D-glucopyranoside) decreased compared to wild-type, kcat (2-nitrophenyl beta-D-glucopyranoside) decreased. Relative efficacy toward (2-nitrophenyl beta-D-glucopyranoside) similar to wild-type. Km (dhurrin) similar to wild-type, kcat drastically decreased Sorghum bicolor
3.2.1.21 D261N the D261N substitution leads to a drastic decrease in relative efficiency of ZmGlu1 on all substrates tested, but little effect on the Km Zea mays
3.2.1.21 F198V mutant shows drastic effect on catalytic efficacy, kcat is reduced by 90% for hydrolysis of 4-methylumbelliferyl beta-D-glucopyranoside compared to wild-type. Mutant is unable to hydrolyze 4-nitrophenyl beta-D-glucopyranoside. Only negligible activity toward substrate 2-nitrophenyl beta-D-glucopyranoside compared to wild-type Zea mays
3.2.1.21 F198V/F205L/P377A mutant shows a drastic reduced relative efficacy for all test substrated due to a decreased turnover Zea mays
3.2.1.21 F205L Mutant shows similar relative efficacy compared to wild-type toward all substrates tested. Mutant shows no significant effect on hydrolysis of 4-nitrophenyl beta-D-glucopyranoside other than doubling the kcat value compared to wild-type Zea mays
3.2.1.21 F466S mutant exhibits a marked increase in relative efficiency in comparison to wild-type ZmGlu1 on all substrates tested (from 28 to 123%), because of increased substrate turnover. Mutant has little effect on dhurrin hydrolysis compared to wild-type (3% of relative efficacy compared to Sorghum Dhr1) Zea mays
3.2.1.21 F466S/A467S the A467S substitution in ZmGlu1 has no detectable effect on substrate specificity and catalytic efficiency in the case of 4-nitrophenyl beta-D-glucopyranoside or 2-nitrophenyl beta-D-glucopyranoside hydrolysis, and only a lower Km is obtained for 4-methylumbelliferyl beta-D-glucuronide compared to mutant F466S. Mutant has little effect on dhurrin hydrolysis compared to wild-type (3% of relative efficacy compared to Sorghum Dhr1) Zea mays
3.2.1.21 F469Y Km (2-nitrophenyl beta-D-glucopyranoside) increased compared to wild-type, kcat (2-nitrophenyl beta-D-glucopyranoside) decreased. Relative efficacy toward (2-nitrophenyl beta-D-glucopyranoside) significantly decreased by factor 2.5. Km (dhurrin) similar to wild-type, kcat drastically decreased Sorghum bicolor
3.2.1.21 M263F mutant shows reduced relative efficacy by 40 to 50% on 4-nitrophenyl beta-D-glucopyranoside and 4-methylumbelliferyl beta-D-glucopyranoside whereas it shows an increase of about 60% relative efficacy on 2-nitrophenyl beta-D-glucopyranoside compared to wild-type Zea mays
3.2.1.21 additional information creation of chimeric mutants (Chim21 and Chim16) which are produced by reciprocal domain-swapping between ZmGlu1 and (Sorghum) SbDhr1: ZmGlu1 hydrolyzes dhurrin with a lower catalytic efficiency only when a C-terminal octapeptide 466-477 is exchanged with the homologous octapeptide of SorghumDhr1 (462-469). This peptide substitution leading to amino acid substitutions at four sites is found in Chim21 and Chim16 (with an extra 22 amino acids substitution) enables ZmGlu1 to hydrolyze dhurrin with less than 10% of the relative efficiency of SorghumDhr1 (7.4% for Chim21 and 9.5% for Chim16) Zea mays
3.2.1.21 P377A P377A mutation leads to changes (decreases) in both kcat and Km for all substrated with no decrease in the overall relative efficiency Zea mays
3.2.1.21 V196F/L203F Km (2-nitrophenyl beta-D-glucopyranoside) decreased compared to wild-type, kcat (2-nitrophenyl beta-D-glucopyranoside) decreased. Relative efficacy toward (2-nitrophenyl beta-D-glucopyranoside) similar to wild-type. Km (dhurrin) similar to wild-type, kcat drastically decreased Sorghum bicolor
3.2.1.21 Y473F kcat is increased by 110% to 450% depending on the substrate tested. Enhanced turnover is compensated by a slight increase in Km of this mutant giving a 40% to 250% (depending on the substrate tested) better relative efficacy over the wild-type enzyme. Mutation leads to a significant effect towards dhurrin hydrolysis (10% relative efficacy as compared to Sorghum Dhr1) Zea mays

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.2.1.21 Dhurrin competitive inhibitor Zea mays

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.2.1.21 0.031
-
 Dhurrin pH 5.8, 37°C, mutant F205L Zea mays
3.2.1.21 0.047
-
 Dhurrin pH 5.8, 37°C, mutant Y473F Zea mays
3.2.1.21 0.058
-
 Dhurrin pH 5.8, 37°C, mutant F198V/F205L/P377A Zea mays
3.2.1.21 0.06
-
 Dhurrin pH 5.8, 37°C, mutant A375P Sorghum bicolor
3.2.1.21 0.061
-
 Dhurrin pH 5.8, 37°C, wild-type Sorghum bicolor
3.2.1.21 0.065
-
 Dhurrin pH 5.8, 37°C, mutant F466S/A467S Zea mays
3.2.1.21 0.065
-
 Dhurrin pH 5.8, 37°C, mutant V196F/L203F Sorghum bicolor
3.2.1.21 0.066
-
 Dhurrin pH 5.8, 37°C, mutant M263F Zea mays
3.2.1.21 0.076
-
 Dhurrin pH 5.8, 37°C, chimeric mutant (Chim21) bearing a C-terminal octapeptide (466-477) exchanged with the homologous octapeptide of Sorghum Dhr1 Zea mays
3.2.1.21 0.092
-
 Dhurrin pH 5.8, 37°C, mutant F466S Zea mays
3.2.1.21 0.101
-
 Dhurrin pH 5.8, 37°C, chimeric mutant (Chim16) bearing a C-terminal octapeptide (466-477) exchanged with the homologous octapeptide of Sorghum Dhr1 (with an extra 22 amino acids substitution) Zea mays
3.2.1.21 0.127
-
 Dhurrin pH 5.8, 37°C, mutant F469Y Sorghum bicolor
3.2.1.21 0.16
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant P377A Zea mays
3.2.1.21 0.23
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F198V Zea mays
3.2.1.21 0.33
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F198V/F205L/P377A Zea mays
3.2.1.21 0.37
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, wild-type Zea mays
3.2.1.21 0.395
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F205L Zea mays
3.2.1.21 0.41
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant M263F Zea mays
3.2.1.21 0.42
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant D261N Zea mays
3.2.1.21 0.43
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant M263F Zea mays
3.2.1.21 0.45
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant P377A Zea mays
3.2.1.21 0.49
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F466S Zea mays
3.2.1.21 0.55
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant Y473F Zea mays
3.2.1.21 0.625
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F205L Zea mays
3.2.1.21 0.64
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, wild-type Zea mays
3.2.1.21 0.76
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F466S/A467S Zea mays
3.2.1.21 0.9
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant D261N Zea mays
3.2.1.21 0.94
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F198V/F205L/P377A Zea mays
3.2.1.21 1.04
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant Y473F Zea mays
3.2.1.21 1.06
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F466S Zea mays
3.2.1.21 1.15
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F466S/A467S Zea mays
3.2.1.21 1.21
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant M263F Zea mays
3.2.1.21 1.22
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F198V Zea mays
3.2.1.21 1.24
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant P377A Zea mays
3.2.1.21 1.65
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, wild-type Zea mays
3.2.1.21 1.7
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant D261N Zea mays
3.2.1.21 1.85
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant Y473F Zea mays
3.2.1.21 1.86
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F205L Zea mays
3.2.1.21 1.87
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F466S Zea mays
3.2.1.21 1.88
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F466S/A467S Zea mays
3.2.1.21 2.72
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant A375P Sorghum bicolor
3.2.1.21 2.81
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant V196F/L203F Sorghum bicolor
3.2.1.21 3.76
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F198V/F205L/P377A Zea mays
3.2.1.21 3.83
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, wild-type Sorghum bicolor
3.2.1.21 5.51
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F469Y Sorghum bicolor

Organism

EC Number Organism UniProt Comment Textmining
3.2.1.21 Sorghum bicolor
-
-
-
3.2.1.21 Zea mays P49235
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
3.2.1.21 using Ni-NTA chromatography Sorghum bicolor
3.2.1.21 using Ni-NTA chromatography Zea mays

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.2.1.21 2-nitrophenyl beta-D-glucopyranoside + H2O
-
 Sorghum bicolor 2-nitrophenol + beta-D-glucose
-
 ?
3.2.1.21 2-nitrophenyl beta-D-glucopyranoside + H2O
-
 Zea mays 2-nitrophenol + beta-D-glucose
-
 ?
3.2.1.21 4-methylumbelliferyl beta-D-glucopyranoside + H2O
-
 Zea mays 4-methylumbelliferone + beta-D-glucose
-
 ?
3.2.1.21 4-nitrophenyl beta-D-glucopyranoside + H2O
-
 Zea mays 4-nitrophenol + beta-D-glucose
-
 ?
3.2.1.21 dhurrin + H2O
-
 Sorghum bicolor (2S)-hydroxy(4-hydroxyphenyl)ethanenitrile + beta-D-glucose
-
 ?
3.2.1.21 dhurrin + H2O
-
 Zea mays (2S)-hydroxy(4-hydroxyphenyl)ethanenitrile + beta-D-glucose
-
 ?

Subunits

EC Number Subunits Comment Organism
3.2.1.21 homodimer crystal structure Zea mays

Synonyms

EC Number Synonyms Comment Organism
3.2.1.21 SbDhr1
-
 Sorghum bicolor
3.2.1.21 ZmGlu1
-
 Zea mays

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.2.1.21 37
-
 assay at Sorghum bicolor
3.2.1.21 37
-
 assay at Zea mays

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
3.2.1.21 0.16
-
 Dhurrin pH 5.8, 37°C, mutant F205L Zea mays
3.2.1.21 0.21
-
 Dhurrin pH 5.8, 37°C, mutant M263F Zea mays
3.2.1.21 0.55
-
 Dhurrin pH 5.8, 37°C, mutant F466S/A467S Zea mays
3.2.1.21 0.59
-
 Dhurrin pH 5.8, 37°C, mutant F466S Zea mays
3.2.1.21 0.67
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F198V/F205L/P377A Zea mays
3.2.1.21 0.7
-
 Dhurrin pH 5.8, 37°C, mutant F198V/F205L/P377A Zea mays
3.2.1.21 1.13
-
 Dhurrin pH 5.8, 37°C, mutant Y473F Zea mays
3.2.1.21 1.32
-
 Dhurrin pH 5.8, 37°C, chimeric mutant (Chim21) bearing a C-terminal octapeptide (466-477) exchanged with the homologous octapeptide of Sorghum Dhr1 Zea mays
3.2.1.21 1.7
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F198V/F205L/P377A Zea mays
3.2.1.21 2.23
-
 Dhurrin pH 5.8, 37°C, chimeric mutant (Chim16) bearing a C-terminal octapeptide (466-477) exchanged with the homologous octapeptide of Sorghum Dhr1 (with an extra 22 amino acids substitution) Zea mays
3.2.1.21 3.4
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F198V Zea mays
3.2.1.21 3.6
-
 Dhurrin pH 5.8, 37°C, mutant A375P Sorghum bicolor
3.2.1.21 3.7
-
 Dhurrin pH 5.8, 37°C, mutant V196F/L203F Sorghum bicolor
3.2.1.21 4.97
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant D261N Zea mays
3.2.1.21 6.52
-
 Dhurrin pH 5.8, 37°C, mutant F469Y Sorghum bicolor
3.2.1.21 6.6
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F198V Zea mays
3.2.1.21 9.2
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F469Y Sorghum bicolor
3.2.1.21 10.1
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant V196F/L203F Sorghum bicolor
3.2.1.21 10.85
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant P377A Zea mays
3.2.1.21 11.1
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant M263F Zea mays
3.2.1.21 11.4
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant A375P Sorghum bicolor
3.2.1.21 13.8
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, wild-type Sorghum bicolor
3.2.1.21 14.3
-
 Dhurrin pH 5.8, 37°C, wild-type Sorghum bicolor
3.2.1.21 16.8
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant P377A Zea mays
3.2.1.21 17.2
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant D261N Zea mays
3.2.1.21 17.8
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant M263F Zea mays
3.2.1.21 19.1
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F198V/F205L/P377A Zea mays
3.2.1.21 29.5
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, wild-type Zea mays
3.2.1.21 30.3
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, wild-type Zea mays
3.2.1.21 34.3
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F205L Zea mays
3.2.1.21 36.4
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant D261N Zea mays
3.2.1.21 57.3
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F205L Zea mays
3.2.1.21 63.4
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant Y473F Zea mays
3.2.1.21 74.4
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant P377A Zea mays
3.2.1.21 87.2
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F466S/A467S Zea mays
3.2.1.21 97.9
-
 4-methylumbelliferyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F466S Zea mays
3.2.1.21 100.7
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F466S Zea mays
3.2.1.21 118.5
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F466S/A467S Zea mays
3.2.1.21 121.5
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, wild-type Zea mays
3.2.1.21 137.3
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F205L Zea mays
3.2.1.21 143.8
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant M263F Zea mays
3.2.1.21 163.8
-
 4-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant Y473F Zea mays
3.2.1.21 172.4
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F466S Zea mays
3.2.1.21 177.1
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant F466S/A467S Zea mays
3.2.1.21 353.2
-
 2-nitrophenyl beta-D-glucopyranoside pH 5.8, 37°C, mutant Y473F Zea mays

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.2.1.21 5.8
-
 assay at Sorghum bicolor
3.2.1.21 5.8
-
 assay at Zea mays