2-Hydroxymuconate semialdehyde

2-Hydroxymuconate semialdehyde
Names
Preferred IUPAC name
(2Z,4E)-2-Hydroxy-6-oxohexa-2,4-dienoic acid
Other names
hydroxymuconic semialdehyde; 2-hydroxymuconate semialdehyde; 2-hydroxymuconate-6-semialdehyde
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C6H6O4/c7-4-2-1-3-5(8)6(9)10/h1-4,8H,(H,9,10)/b2-1-,5-3+ checkY
    Key: KGLCZTRXNNGESL-REDYYMJGSA-N checkY
  • O=C/C=C\C=C(\O)C(=O)O
Properties
C6H6O4
Molar mass 142.110 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

2-Hydroxymuconate semialdehyde is formed from catechol by the enzyme catechol 2,3-dioxygenase during the degradation of benzoates.[1][2]

2D representation of the chemical structure of catechol .
catechol
 
O2
 
Reversible left-right reaction arrow with minor forward substrate(s) from top left and minor reverse product(s) to bottom left
O2
 
 
2D representation of the chemical structure of Q27135627.
2-hydroxymuconate semialdehyde

It is oxidised to (2E,4Z)-2-hydroxymuconic acid] by the enzyme 2-hydroxymuconate-6-semialdehyde dehydrogenase.[3]

2D representation of the chemical structure of Q27135627.
2-hydroxymuconate semialdehyde
+ NAD+
 
 
H2O
H+
Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left
H2O
H+
 
2D representation of the chemical structure of Q27132982.
(2E,4Z)-2-hydroxymuconic acid
+ NADH
 

It is also degraded into formate and 2-oxopent-4-enoic acid by 2-hydroxymuconate-semialdehyde hydrolase.[4]

2D representation of the chemical structure of Q27135627.
2-hydroxymuconate semialdehyde
 
H2O
HCO2H
Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left
H2O
HCO2H
 
2D representation of the chemical structure of 2-Oxopent-4-enoic acid.
2-oxopent-4-enoic acid

References

  1. ^ Sala-Trepat JM, Evans WC (1971). "The meta cleavage of catechol by Azotobacter species 4-Oxalocrotonate pathway". Eur. J. Biochem. 20 (3): 400–13. doi:10.1111/j.1432-1033.1971.tb01406.x. PMID 4325686.
  2. ^ Enzyme 1.13.11.2 at KEGG Pathway Database.
  3. ^ Kasai D, Fujinami T, Abe T, Mase K, Katayama Y, Fukuda M, Masai E (November 2009). "Uncovering the protocatechuate 2,3-cleavage pathway genes". Journal of Bacteriology. 191 (21): 6758–68. doi:10.1128/JB.00840-09. PMC 2795304. PMID 19717587.
  4. ^ Sala-Trepat JM, Evans WC (1971). "The meta cleavage of catechol by Azotobacter species 4-Oxalocrotonate pathway". European Journal of Biochemistry. 20 (3): 400–13. doi:10.1111/j.1432-1033.1971.tb01406.x. PMID 4325686.
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