Biology:4-Hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase

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Short description: Class of enzymes
4-Hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase
Identifiers
EC number3.2.1.182
Databases
IntEnzIntEnz view
BRENDABRENDA entry
ExPASyNiceZyme view
KEGGKEGG entry
MetaCycmetabolic pathway
PRIAMprofile
PDB structuresRCSB PDB PDBe PDBsum

4-Hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase (EC 3.2.1.182, DIMBOAGlc hydrolase, DIMBOA glucosidase) is an enzyme with systematic name (2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside beta-D-glucosidase.[1][2][3][4][5][6] This enzyme catalyses the following chemical reaction

(1) (2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside + H2O [math]\displaystyle{ \rightleftharpoons }[/math] 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one + D-glucose
(2) (2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside + H2O [math]\displaystyle{ \rightleftharpoons }[/math] 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one + D-glucose

The enzyme from Triticum aestivum (wheat) has a higher affinity for DIMBOA glucoside than DIBOA glucoside.

References

  1. "Purification and characterization of a hydroxamic acid glucoside beta-glucosidase from wheat (Triticum aestivum L.) seedlings". Planta 210 (3): 432–8. February 2000. doi:10.1007/s004250050029. PMID 10750901. 
  2. "Purification and characterization of a beta-glucosidase from rye (Secale cereale L.) seedlings". Plant Science 155 (1): 67–74. June 2000. doi:10.1016/s0168-9452(00)00204-1. PMID 10773341. 
  3. "The mechanism of substrate (aglycone) specificity in beta -glucosidases is revealed by crystal structures of mutant maize beta -glucosidase-DIMBOA, -DIMBOAGlc, and -dhurrin complexes". Proceedings of the National Academy of Sciences of the United States of America 97 (25): 13555–60. December 2000. doi:10.1073/pnas.97.25.13555. PMID 11106394. Bibcode2000PNAS...9713555C. 
  4. "Cloning of a plastidic rye (Secale cereale) β-glucosidase cDNA and its expression in Escherichia coli". Physiol. Plant. 118 (3): 337–348. 2003. doi:10.1034/j.1399-3054.2003.00118.x. 
  5. "Molecular and structural characterization of hexameric beta-D-glucosidases in wheat and rye". Plant Physiology 141 (4): 1237–47. August 2006. doi:10.1104/pp.106.077693. PMID 16751439. 
  6. "Active-site architecture of benzoxazinone-glucoside β-D-glucosidases in Triticeae". Plant Science 180 (2): 268–75. February 2011. doi:10.1016/j.plantsci.2010.09.001. PMID 21421370. 

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