CHEBI:67205 - (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid

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ChEBI Name (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid ChEBI ID CHEBI:67205 ChEBI ASCII Name (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid Definition The dicarboxylic acid that is 2,3,4,5-tetrahydrodipicolinic acid hydroxylated at C-4 and with configuration 2S,4S. Stars This entity has been manually annotated by the ChEBI Team. Supplier Information No supplier information found for this compound. Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Formula C7H9NO5 Net Charge 0 Average Mass 187.15010 Monoisotopic Mass 187.04807 InChI InChI=1S/C7H9NO5/c9-3-1-4(6(10)11)8-5(2-3)7(12)13/h3-4,9H,1-2H2,(H,10,11)(H,12,13)/t3-,4-/m0/s1 InChIKey DVTPRYHENFBCII-IMJSIDKUSA-N SMILES O[C@H]1C[C@H](N=C(C1)C(O)=O)C(O)=O Roles Classification Chemical Role(s): Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid ) View more via ChEBI Ontology ChEBI Ontology Outgoing (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid (CHEBI:67205) has functional parent dipicolinic acid (CHEBI:46837) (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid (CHEBI:67205) is a dicarboxylic acid (CHEBI:35692) (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid (CHEBI:67205) is conjugate acid of (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate(2−) (CHEBI:67139) Incoming (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate(2−) (CHEBI:67139) is conjugate base of (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid (CHEBI:67205) IUPAC Name (2S,4S)-4-hydroxy-2,3,4,5-tetrahydropyridine-2,6-dicarboxylic acid Synonym Source (4S)-4-hydroxy-2,3,4,5-tetrahydro-(2S)-dipicolinic acid ChEBI Registry Number Type Source 21027218 Reaxys Registry Number Reaxys Citation Blickling S, Renner C, Laber B, Pohlenz HD, Holak TA, Huber R (1997) Reaction mechanism of Escherichia coli dihydrodipicolinate synthase investigated by X-ray crystallography and NMR spectroscopy. Biochemistry 36, 24-33 [PubMed:8993314] [show Abstract] Dihydrodipicolinate synthase (DHDPS) catalyzes the condensation of pyruvate with L-aspartate beta-semialdehyde. It is the first enzyme unique to the diaminopimelate pathway of lysine biosynthesis. Here we present the crystal structures of five complexes of Escherichia coli DHDPS with substrates, substrate analogs, and inhibitors. These include the complexes of DHDPS with (1) pyruvate, (2) pyruvate and the L-aspartate beta-semialdehyde analog succinate beta-semialdehyde, (3) the inhibitor alpha-ketopimelic acid, (4) dipicolinic acid, and (5) the natural feedback inhibitor L-lysine. The kinetics of inhibition were determined, and the binding site of the L-lysine was identified. NMR experiments were conducted in order to elucidate the nature of the product of the reaction catalyzed by DHDPS. By this method, (4S)-4-hydroxy-2,3,4,5-tetrahydro-(2S)-dipicolinic acid is identified as the only product. A reaction mechanism for DHDPS is proposed, and important features for inhibition are identified. Last Modified 24 August 2012