Wikipedia

Succinic semialdehyde

Succinic semialdehyde (SSA) is a GABA and GHB metabolite. It is formed from GABA by the action of GABA transaminase (4-aminobutyrate aminotransferase) and further oxidised to become succinic acid, which enters TCA cycle. SSA is oxidized into succinic acid by the enzyme succinic semialdehyde dehydrogenase, which uses NAD as a cofactor.[2] [3]  When the oxidation of succinic semialdehyde to succinic acid is impaired, accumulation of succinic semialdehyde takes place which leads to succinic semialdehyde dehydrogenase deficiency.[3]

Succinic semialdehyde
Names
Preferred IUPAC name
4-Oxobutanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.155.728 Edit this at Wikidata
KEGG
MeSH Succinic semialdehyde
UNII
  • InChI=1S/C4H6O3/c5-3-1-2-4(6)7/h3H,1-2H2,(H,6,7) checkY
    Key: UIUJIQZEACWQSV-UHFFFAOYSA-N checkY
  • InChI=1/C4H6O3/c5-3-1-2-4(6)7/h3H,1-2H2,(H,6,7)
    Key: UIUJIQZEACWQSV-UHFFFAOYAS
  • O=CCCC(=O)O
Properties
C4H6O3
Molar mass 102.089 g/mol
Appearance oil
Boiling point 135 °C (275 °F; 408 K) at 14 mmHg
soluble in water, ethanol, benzene, diethyl ether[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

In addition to the pathway involving GABA transaminase, gamma-hydroxybutyric acid (GHB) can also be metabolized to SSA via GHB dehydrogenase or by GHB transhydrogenase (D-2-hydroxyglutarate transhydrogenase).[4][5][6][7]

See also

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References

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  1. ^ Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 3–446, ISBN 0-8493-0863-23-446&rft.edition=87&rft.pub=CRC Press&rft.date=1998&rft.isbn=0-8493-0863-2&rft.aulast=Lide&rft.aufirst=David R.&rfr_id=info:sid/en.wikipedia.org:Succinic semialdehyde" class="Z3988">
  2. ^ Peng, Qi; Yang, Min; Wang, Wei; Han, Lili; Wang, Guannan; Wang, Pengyue; Zhang, Jie; Song, Fuping (2014-12-20). "Activation of gab cluster transcription in Bacillus thuringiensis by γ-aminobutyric acid or succinic semialdehyde is mediated by the Sigma 54-dependent transcriptional activator GabR". BMC Microbiology. 14 (1): 306. doi:10.1186/s12866-014-0306-3. ISSN 1471-2180. PMC 4279683. PMID 25527261.
  3. ^ a b Struys, E. A.; Jansen, E. E. W.; Gibson, K. M.; Jakobs, C. (December 2005). "Determination of the GABA analogue succinic semialdehyde in urine and cerebrospinal fluid by dinitrophenylhydrazine derivatization and liquid chromatography–tandem mass spectrometry: Application to SSADH deficiency". Journal of Inherited Metabolic Disease. 28 (6): 913–920. doi:10.1007/s10545-005-0111-0. ISSN 0141-8955. PMID 16435183. S2CID 9956364.913-920&rft.date=2005-12&rft.issn=0141-8955&rft_id=https://api.semanticscholar.org/CorpusID:9956364#id-name=S2CID&rft_id=info:pmid/16435183&rft_id=info:doi/10.1007/s10545-005-0111-0&rft.aulast=Struys&rft.aufirst=E. A.&rft.au=Jansen, E. E. W.&rft.au=Gibson, K. M.&rft.au=Jakobs, C.&rft_id=https://onlinelibrary.wiley.com/doi/10.1007/s10545-005-0111-0&rfr_id=info:sid/en.wikipedia.org:Succinic semialdehyde" class="Z3988">
  4. ^ Busardò FP, Jones AW (January 2015). "GHB pharmacology and toxicology: acute intoxication, concentrations in blood and urine in forensic cases and treatment of the withdrawal syndrome". Current Neuropharmacology. 13 (1): 47–70. doi:10.2174/1570159X13666141210215423. PMC 4462042. PMID 26074743.47-70&rft.date=2015-01&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4462042#id-name=PMC&rft_id=info:pmid/26074743&rft_id=info:doi/10.2174/1570159X13666141210215423&rft.aulast=Busardò&rft.aufirst=FP&rft.au=Jones, AW&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4462042&rfr_id=info:sid/en.wikipedia.org:Succinic semialdehyde" class="Z3988">
  5. ^ Felmlee MA, Morse BL, Morris ME (January 2021). "γ-Hydroxybutyric Acid: Pharmacokinetics, Pharmacodynamics, and Toxicology". The AAPS Journal. 23 (1): 22. doi:10.1208/s12248-020-00543-z. PMC 8098080. PMID 33417072.
  6. ^ Taxon ES, Halbers LP, Parsons SM (May 2020). "Kinetics aspects of Gamma-hydroxybutyrate dehydrogenase". Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics. 1868 (5): 140376. doi:10.1016/j.bbapap.2020.140376. PMID 31981617.
  7. ^ Kamal RM, van Noorden MS, Franzek E, Dijkstra BA, Loonen AJ, De Jong CA (March 2016). "The Neurobiological Mechanisms of Gamma-Hydroxybutyrate Dependence and Withdrawal and Their Clinical Relevance: A Review". Neuropsychobiology. 73 (2): 65–80. doi:10.1159/000443173. hdl:2066/158441. PMID 27003176.65-80&rft.date=2016-03&rft_id=info:hdl/2066/158441&rft_id=info:pmid/27003176&rft_id=info:doi/10.1159/000443173&rft.aulast=Kamal&rft.aufirst=RM&rft.au=van Noorden, MS&rft.au=Franzek, E&rft.au=Dijkstra, BA&rft.au=Loonen, AJ&rft.au=De Jong, CA&rfr_id=info:sid/en.wikipedia.org:Succinic semialdehyde" class="Z3988">
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