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Ligand DIMBOA-glucoside

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

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Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.2.1.21

2-O-beta-D-glucopyranosyl-4-hydroxy-7-methoxy-1,4-benzoxazin-3-one + H2O = 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one + beta-D-glucose

665542

-

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.202

UDP-glucose + 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one = UDP + 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-D-glucoside

0

-

Substrate in Enzyme-catalyzed Reactions (8 results)

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Show Substrate (8 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.2.1.182

2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one beta-D-glucopyranoside + H2O = 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one + beta-D-glucose

657120

-

3.2.1.182

DIMBOA beta-D-glucoside + H2O = DIMBOA + beta-D-glucose

720627

-

3.2.1.182

DIMBOA-beta-D-glucoside + H2O = DIMBOA + beta-D-glucose

720762

-

3.2.1.182

DIMBOA-glucoside + H2O = DIMBOA + beta-D-glucose

682403, 719801, 720757, 721120, 721121, 720759, 720952, 720762

-

3.2.1.21

2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one glucoside + H2O = 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one + beta-D-glucose

657120

-

3.2.1.21

2-O-beta-D-glucopyranosyl-4-hydroxy-7-methoxy-1,4-benzoxazin-3-one + H2O = 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one + beta-D-glucose

682403

-

3.2.1.21

2-O-beta-D-glucopyranosyl-4-hydroxy-7-methoxy-1,4-benzoxazin-3-one + H2O = 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one + beta-D-glucose

665542

-

3.2.1.21

DIMBOA-glucoside + H2O = ?

723386

-

3.2.1.182

4 entries

3.2.1.21

4 entries

Product in Enzyme-catalyzed Reactions (1 result)

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Show Product (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.202

UDP-glucose + 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one = UDP + 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-D-glucoside

0, 637794

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (16 results)

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Show Turnover Number (16 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

3.2.1.182

19.54

-

pH 5.8, 37°C, mutant Chim16 (chimeric construct: parental Zea mays Glu1 with exchanged domain 466-495 of Sorghum Dhr1)

719801

3.2.1.182

20.15

-

pH 5.8, 37°C, mutant Chim21 (chimeric construct: parental Zea mays Glu1 with exchanged domain 466-473 of Sorghum Dhr1)

719801

3.2.1.182

24.02

-

pH 5.8, 37°C, mutant Chim15 (chimeric construct: parental Zea mays Glu1 with exchanged domain 496-518 of Sorghum Dhr1)

719801

3.2.1.182

25.67

-

pH 5.8, 37°C, mutant Chim22 (chimeric construct: parental Zea mays Glu1 with exchanged domain 481-490 of Sorghum Dhr1)

719801

3.2.1.182

29.16

-

pH 5.8, 37°C, wild-type

719801

3.2.1.182

43.33

-

pH 5.8, 37°C, mutant Chim2 (chimeric construct: parental Zea mays Glu1 with exchanged domain 466-518 of Sorghum Dhr1)

719801

3.2.1.182

73.3

-

pH 5.5, 30°C, mutant S464F

682403

3.2.1.182

85.1

-

pH 5.5, 30°C, mutant Y378F

682403

3.2.1.182

97.4

-

pH 5.8, 37°C, recombinant protein

720627

3.2.1.182

110

-

pH 5.5, 30°C, mutant F198A

682403

3.2.1.182

119

-

pH 5.8, 37°C, native protein

720627

3.2.1.182

124

-

pH 5.5, 30°C, mutant Y378A

682403

3.2.1.182

192

-

pH 5.5, 30°C, mutant F471Y

682403

3.2.1.182

338

-

pH 5.5, 30°C, wild-type

682403

3.2.1.182

773

-

pH 5.5, 30°C, wild-type

682403

3.2.1.182

1201

-

pH 5.5, 30°C, wild-type

682403

3.2.1.182

16 entries

K_M Value (29 results)

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Show KM Value (29 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.2.1.182

0.07

-

pH and temperature not specified in the publication

721120

3.2.1.182

0.098

-

pH 5.8, 37°C, mutant Chim22 (chimeric construct: parental Zea mays Glu1 with exchanged domain 481-490 of Sorghum Dhr1)

719801

3.2.1.182

0.098

-

pH 5.8, 37°C, wild-type

719801

3.2.1.182

0.104

-

pH 5.8, 37°C, mutant Chim21 (chimeric construct: parental Zea mays Glu1 with exchanged domain 466-473 of Sorghum Dhr1)

719801

3.2.1.182

0.106

-

pH 5.8, 37°C, mutant Chim15 (chimeric construct: parental Zea mays Glu1 with exchanged domain 496-518 of Sorghum Dhr1)

719801

3.2.1.182

0.13

-

pH 5.5, 30°C, mutant Y378F

682403

3.2.1.182

0.16

-

pH and temperature not specified in the publication

721121

3.2.1.182

0.2

-

pH 5.8, 37°C, mutant Chim16 (chimeric construct: parental Zea mays Glu1 with exchanged domain 466-495 of Sorghum Dhr1)

719801

3.2.1.182

0.205

-

pH 5.8, 37°C, mutant Chim2 (chimeric construct: parental Zea mays Glu1 with exchanged domain 466-518 of Sorghum Dhr1)

719801

3.2.1.182

0.27

-

pH 5.5, 30°C

657120

3.2.1.182

0.29

-

pH 5.5, 30°C, wild-type

682403

3.2.1.182

0.36

-

pH 5.5, 30°C, wild-type

682403

3.2.1.182

0.39

-

pH 5.5, 30°C, wild-type

682403

3.2.1.182

0.59

-

pH 5.5, 30°C, mutant G464S/S465L

682403

3.2.1.182

0.617

-

pH 5.5, 25°C

720759

3.2.1.182

0.7

-

pH 5.5, 30°C, mutant F471Y

682403

3.2.1.182

0.76

-

pH 5.5, 30°C, mutant S465L

682403

3.2.1.182

0.94

-

pH 5.5, 30°C, mutant G464S

682403

3.2.1.182

1.04

-

pH 5.5, 30°C, mutant F471Y

682403

3.2.1.182

1.07

-

pH 5.5, 30°C, mutant Y378F

682403

3.2.1.182

1.19

-

pH 5.5, 30°C, mutant Y378A

682403

3.2.1.182

1.3

-

pH 5.5, 30°C, wild-type

682403

3.2.1.182

1.4

-

pH 5.8, 37°C, recombinant protein

720627

3.2.1.182

1.42

-

pH 5.5, 30°C, mutant S464F

682403

3.2.1.182

1.42

-

pH 5.5, 30°C, mutant Y378A

682403

3.2.1.182

2.1

-

pH 5.8, 37°C, native protein

720627

3.2.1.182

5.12

-

pH 5.5, 30°C, mutant G464F

682403

3.2.1.182

35.7

-

pH 5.5, 30°C, mutant F198A

682403

3.2.1.182

39.3

-

pH 5.5, 30°C, mutant F198A

682403

3.2.1.182

29 entries

References & Links

Literature References (13)

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Show Reference (13 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

637794

16666853

Hydroxamic acid glucosyltransferases from maize seedlings

1989

Bailey, B.A.; Larson, R.L.

Plant Physiol.

90

1071-1076

657120

10750901

Purification and characterization of a hydroxamic acid glucoside beta-glucosidase from wheat (Triticum aestivum L.) seedlings

2000

Sue, M.; Ishihara, A.; Iwamura, H.

Planta

210

432-438

665542

15148317

Structural determinants of substrate specificity in family 1 beta-glucosidases: novel insights from the crystal structure of sorghum dhurrinase-1, a plant beta-glucosidase with strict specificity, in complex with its natural substrate

2004

Verdoucq, L.; Moriniere, J.; Bevan, D.R.; Esen, A.; Vasella, A.; Henrissat, B.; Czjze, M.

J. Biol. Chem.

279

31796-31803

682403

16751439

Molecular and structural characterization of hexameric beta-D-glucosidases in wheat and rye

2006

Sue, M.; Yamazaki, K.; Yajima, S.; Nomura, T.; Matsukawa, T.; Iwamura, H.; Miyamoto, T.

Plant Physiol.

141

1237-1247

719801

10748038

The aglycone specificity-determining sites are different in 2, 4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA)-glucosidase (Maize beta -glucosidase) and dhurrinase (Sorghum beta -glucosidase)

2000

Cicek, M.; Blanchard, D.; Bevan, D.R.; Esen, A.

J. Biol. Chem.

275

20002-20011

720627

-

Cloning of a plastidic rye (Secale cereale) beta-glucosidase cDNA and its expression in Escherichia coli

2003

Nikus, J.; Esen, A.; Jonsson, L.

Physiol. Plant.

118

337-345

720757

-

Substrate specificity of maize beta-glucosidase

1994

Babcock, G.; Esen, A.

Plant Sci.

101

31-39

720759

10773341

Purification and characterization of a beta-glucosidase from rye (Secale cereale L.) seedlings

2000

Sue, M.; Ishihara, A.; Iwamura, H.

Plant sci.

155

67-74

720762

21421370

Active-site architecture of benzoxazinone-glucoside beta-D-glucosidases in Triticeae

2011

Sue, M.; Nakamura, C.; Miyamoto, T.; Yajima, S.

Plant Sci.

180

268-275

720952

11106394

The mechanism of substrate (aglycone) specificity in beta -glucosidases is revealed by crystal structures of mutant maize beta -glucosidase-DIMBOA, -DIMBOAGlc, and -dhurrin complexes

2000

Czjzek, M.; Cicek, M.; Zamboni, V.; Bevan, D.R.; Henrissat, B.; Esen, A.

Proc. Natl. Acad. Sci. USA

97

13555-13560

721120

-

Occurrence of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) and a beta-glucosidase specific for its glucoside in maize seedlings

1998

Ebisui, K.; Ishihara, A.; Hirai, N.; Iwamura, H.

Z. Naturforsch. C

53

793-798

721121

-

Purification and characterization of a beta-glucosidase specific for 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) glucoside in maize

1999

Oikawa, A.; Ebisui, K.; Sue, M.; Ishihara, A.; Iwamura, H.

Z. Naturforsch. C

54

181-185

723386

19965874

Scopolin-hydrolyzing beta-glucosidases in roots of Arabidopsis

2010

Ahn, Y.O.; Shimizu, B.; Sakata, K.; Gantulga, D.; Zhou, C.; Zhou, Z.; Bevan, D.R.; Esen, A.

Plant Cell Physiol.

51

132-43

Links to other databases for DIMBOA-glucoside

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ChEBI

PubChem