Glutamate-5-semialdehyde

{{Chembox

| ImageFile = Glutamate-5-semialdehyde.svg

| ImageSize = 200px

| IUPACName = (2S)-2-Amino-5-oxopentanoic acid

| OtherNames = L-Glutamate gamma-semialdehyde; gamma-Glutamyl semialdehyde

| Section1 = {{Chembox Identifiers

| CASNo = 2886-91-1

| CASNo_Ref = {{cascite|correct|CAS}}

| ChEBI = 17232

| ChemSpiderID = 167744

| DrugBank = DB04388

| KEGG = C01165

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = B517ZPX7HX

| PubChem = 193305

| SMILES = C(C[C@@H](C(=O)O)N)C=O

| InChI=1S/C5H9NO3/c6-4(5(8)9)2-1-3-7/h3-4H,1-2,6H2,(H,8,9)/t4-/m0/s1

| InChIKey= KABXUUFDPUOJMW-BYPYZUCNSA-N

}}

| Section2 = {{Chembox Properties

| C=5|H=9|N=1|O=3

}}

}}

Glutamate-5-semialdehyde is a non-proteinogenic amino acid involved in both the biosynthesis and degradation of proline and arginine (via ornithine),{{cite journal | author = Baich A | date = 1971 | title = The Biosynthesis of Proline in Escherichia coli: Phosphate-Dependent Glutamate-semialdehyde Dehydrogenase (NADP), the Second Enzyme in the Pathway | journal = Biochim. Biophys. Acta | volume = 244 | pages = 129–34 | pmid = 4399189 | issue = 1 | doi=10.1016/0304-4165(71)90129-2}}{{Cite book |last=Voet |first=Donald |url=https://www.worldcat.org/oclc/690489261 |title=Biochemistry |date=2011 |publisher=John Wiley & Sons |others=Judith G. Voet |isbn=978-0-470-57095-1 |edition=4th |location=Hoboken, NJ |oclc=690489261}} 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.{{cite journal |doi=10.1007/s00726-003-0012-1 |title=Recent Advances in the Analysis of Oxidized Proteins |year=2003 |last1=Requena |first1=J. R. |last2=Levine |first2=R. L. |last3=Stadtman |first3=E. R. |journal=Amino Acids |volume=25 |issue=3–4 |pages=221–226 |pmid=14661085 |s2cid=28837698}}