Glutamate-5-semialdehyde

Glutamate-5-semialdehyde

Names
IUPAC name (2S)-2-Amino-5-oxopentanoic acid
Other names L-Glutamate gamma-semialdehyde; gamma-Glutamyl semialdehyde
Identifiers
CAS Number	2886-91-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17232
ChemSpider	167744
DrugBank	DB04388
KEGG	C01165
PubChem CID	193305
UNII	B517ZPX7HX Y
CompTox Dashboard (EPA)	DTXSID601031870
InChI 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
SMILES C(C[C@@H](C(=O)O)N)C=O
Properties
Chemical formula	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). Infobox references

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. In solution in water, the aldehyde is in chemical equilibrium with (S)-1-pyrroline-5-carboxylic acid and this is the form in which many of its biochemical reactions occur.^[3]

L-glutamate-5-semialdehyde

 

 

 

 

 

 

(S)-1-pyrroline-5-carboxylic acid

Reduction of glutamic acid semialdehyde with sodium borohydride gives hydroxyaminovaleric acid.^[4]