Ligand DL-homocysteic acid

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Basic Ligand Information

Molecular Structure
Picture of DL-homocysteic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C4H9NO5S
DL-homocysteic acid
AZKJDCFQZVEZJK-FOCLMDBBSA-N
Synonyms:
2-amino-4-sulfobutanoic acid, Homocysteate, Homocysteic acid

Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
homocysteate + 2-oxoglutarate = 4-mercapto-2-oxobutanoate + L-glutamate
show the reaction diagram
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DL-homocysteic acid + H2O = ?
show the reaction diagram
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ATP + UDP-N-acetylmuramoyl-L-Ala + DL-homocysteic acid = ADP + phosphate + UDP-N-acetylmuramoyl-L-Ala-DL-homocysteic acid
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
uncompetitive
-
50 mM, 21% inhibition; 50 mM, 23% inhibition
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marked (ca. 64%) decrease of respiratory chain complex I activity in the cerebral cortex of immature rats following seizures induced by bilateral intracerebroventricular infusion of DL-homocysteic acid (600 nanomol/side). Decrease is already evident during the acute phase of seizures (60-90 min after infusion) and persists for at least 20 h after the seizures. Inhibition is selective for complex I since activities of complex II and IV and citrate synthase remain unaffected. Inhibition of complex I activity is not associated with changes in complex I content. Enhanced production of reactive oxygen species by inhibited complex I in mitochondria from DL-homocysteic acid-treated animals. Competitive NMDA receptor antagonist AP7, a selective and potent group II mGluR agonist (2R,4R)-APDC and a highly selective group III mGluR, subtype 8, agonist (S)-3,4-DCPG, significantly reduce the extent of complex I inhibition. The superoxide dismutase mimetic Tempol and a selective peroxynitrite scavenger and decomposition catalyst FeTPPS provide a significant attenuation of complex I inhibition associated with DL-homocysteic acid-induced seizures
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Enzyme Kinetic Parameters

Ki Value (2 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.178
-
-
11.1
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pH 8.0, 37C

References & Links

Links to other databases for DL-homocysteic acid

ChEBI
PubChem
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PubChem