KEGG ENZYME: 3.2.1.182

ENZYME: 3.2.1.182

Entry

EC 3.2.1.182                Enzyme

Name

4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase;
DIMBOAGlc hydrolase;
DIMBOA glucosidase

Class

Hydrolases;
Glycosylases;
Glycosidases, i.e. enzymes that hydrolyse O- and S-glycosyl compounds

Sysname

(2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside beta-D-glucosidase

Reaction(IUBMB)

(1) (2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside + H2O = 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one + D-glucose [RN:R12208];
(2) (2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside + H2O = 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one + D-glucose [RN:R12209]

Reaction(KEGG)

R12208 R12209

Substrate

(2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside [CPD:C04831];
H2O [CPD:C00001];
(2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside [CPD:C15772]

Product

2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one [CPD:C04720];
D-glucose [CPD:C00031];
2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one [CPD:C15770]

Comment

The enzyme from Triticum aestivum (wheat) has a higher affinity for DIMBOA glucoside than DIBOA glucoside. With Secale cereale (rye) the preference is reversed.

History

EC 3.2.1.182 created 2012

Reference

1 [PMID:10750901]

Authors

Sue M, Ishihara A, Iwamura H

Title

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

Journal

Planta 210:432-8 (2000)
DOI:10.1007/s004250050029

Reference

2 [PMID:10773341]

Authors

Sue M, Ishihara A, Iwamura H

Title

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

Journal

Plant Sci 155:67-74 (2000)
DOI:10.1016/S0168-9452(00)00204-1

Reference

3 [PMID:11106394]

Authors

Czjzek M, Cicek M, Zamboni V, Bevan DR, Henrissat B, Esen A

Title

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

Journal

Proc Natl Acad Sci U S A 97:13555-60 (2000)
DOI:10.1073/pnas.97.25.13555

Sequence

[zma:542414]

Reference

Authors

Nikus J, Esen A, Jonsson LMV.

Title

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

Journal

Physiol Plantarum 118:337-348 (2003)

Reference

5 [PMID:16751439]

Authors

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

Title

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

Journal

Plant Physiol 141:1237-47 (2006)
DOI:10.1104/pp.106.077693

Reference

6 [PMID:21421370]

Authors

Sue M, Nakamura C, Miyamoto T, Yajima S

Title

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

Journal

Plant Sci 180:268-75 (2011)
DOI:10.1016/j.plantsci.2010.09.001

Other DBs

ExplorEnz - The Enzyme Database:

3.2.1.182

IUBMB Enzyme Nomenclature:

3.2.1.182

ExPASy - ENZYME nomenclature database:

3.2.1.182

BRENDA, the Enzyme Database:

3.2.1.182

LinkDB

DBGET integrated database retrieval system