Glutamate-5-semialdehyde

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Glutamate-5-semialdehyde
Glutamate-5-semialdehyde.svg
Names
IUPAC name
(2S)-2-Amino-5-oxopentanoic acid
Other names
L-Glutamate gamma-semialdehyde; gamma-Glutamyl semialdehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
KEGG
PubChem CID
UNII
  • InChI=1S/C5H9NO3/c6-4(5(8)9)2-1-3-7/h3-4H,1-2,6H2,(H,8,9)/t4-/m0/s1
    Key: KABXUUFDPUOJMW-BYPYZUCNSA-N
  • C(C[C@@H](C(=O)O)N)C=O
Properties
C5H9NO3
Molar mass 131.131 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Glutamate-5-semialdehyde is a non-proteinogenic amino acid involved in both the biosynthesis and degradation of proline and arginine (via ornithine), [1] [2] as well as in the biosynthesis of antibiotics, such as carbapenems. It is synthesized by the reduction of glutamyl-5-phosphate by glutamate-5-semialdehyde dehydrogenase.

Reduction of glutamic acid semialdehyde with sodium borohydride gives hydroxyaminovaleric acid. [3]

See also

References

  1. ↑ Baich A (1971). "The Biosynthesis of Proline in Escherichia coli: Phosphate-Dependent Glutamate-semialdehyde Dehydrogenase (NADP), the Second Enzyme in the Pathway". Biochim. Biophys. Acta. 244 (1): 129–34. doi:10.1016/0304-4165(71)90129-2. PMID   4399189.
  2. ↑ Voet, Donald (2011). Biochemistry. Judith G. Voet (4th ed.). Hoboken, NJ: John Wiley & Sons. ISBN   978-0-470-57095-1. OCLC   690489261.
  3. ↑ Requena, J. R.; Levine, R. L.; Stadtman, E. R. (2003). "Recent Advances in the Analysis of Oxidized Proteins". Amino Acids. 25 (3–4): 221–226. doi:10.1007/s00726-003-0012-1. PMID   14661085. S2CID   28837698.
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