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 ;
3D model (JSmol)	Interactive image;
PubChem CID	193305;
UNII	B517ZPX7HX ;
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.

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

Glutamate-1-semialdehyde

[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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[1] [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] [2]
Voet, Donald (2011). Biochemistry. Judith G. Voet (4th ed.). Hoboken, NJ: John Wiley & Sons. ISBN 978-0-470-57095-1. OCLC 690489261.

[3] [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.

[1]

[2]

[3]

Glutamate-5-semialdehyde

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References

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
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