Isoglutamine

Isoglutamine
Names
	IUPAC name 4,5-diamino-5-oxopentanoic acid
Identifiers
CAS Number	DL: 328-48-3 ; (S/L): 636-65-7 [DrugBank]; (R/D): 19522-40-8 [EPA];
3D model (JSmol)	DL: Interactive image; (S/L): Interactive image; (R/D): Interactive image;
Abbreviations	IsoGln
ChemSpider	DL: 144380 ;
DrugBank	(S/L): DB03091;
KEGG	DL: C16673;
PubChem CID	DL: 164697; (S/L): 445883; (R/D): 5288447;
UNII	(S/L): WL74QNU57B; (R/D): IY2O406N69;
CompTox Dashboard (EPA)	(R/D): DTXSID90415341;
	InChI InChI=1S/C5H10N2O3/c6-3(5(7)10)1-2-4(8)9/h3H,1-2,6H2,(H2,7,10)(H,8,9) Key: AEFLONBTGZFSGQ-UHFFFAOYSA-N ; DL: InChI=1S/C5H10N2O3/c6-3(5(7)10)1-2-4(8)9/h3H,1-2,6H2,(H2,7,10)(H,8,9); InChI=1/C5H10N2O3/c6-3(5(7)10)1-2-4(8)9/h3H,1-2,6H2,(H2,7,10)(H,8,9) Key: AEFLONBTGZFSGQ-UHFFFAOYAS; (S/L): InChI=1S/C5H10N2O3/c6-3(5(7)10)1-2-4(8)9/h3H,1-2,6H2,(H2,7,10)(H,8,9)/t3-/m0/s1 Key: AEFLONBTGZFSGQ-VKHMYHEASA-N; (R/D): InChI=1S/C5H10N2O3/c6-3(5(7)10)1-2-4(8)9/h3H,1-2,6H2,(H2,7,10)(H,8,9)/t3-/m1/s1 Key: AEFLONBTGZFSGQ-GSVOUGTGSA-N;
	SMILES DL: O=C(N)C(N)CCC(=O)O; (S/L): C(CC(=O)O)[C@@H](C(=O)N)N; (R/D): C(CC(=O)O)[C@H](C(=O)N)N;
Properties
Chemical formula	C5H10N2O3
Molar mass	146.146 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Isoglutamine or α-glutamine is a gamma amino acid derived from glutamic acid by substituting the carboxyl group in position 1 with an amide group.^[1] This is in contrast to the proteinogenic amino acid glutamine, which is the 5-amide of glutamic acid.

Isoglutamine can form the C-terminus of a peptide chain, as in muramyl dipeptide (MDP), a constituent of bacterial cell walls. It can also occur inside a peptide chain, in which case the chain is continued at the carboxyl group and isoglutamine behaves as a γ-amino acid, as in mifamurtide, a synthetic derivative of MDP used to treat osteosarcoma.

Stereochemistry

Substituting l-glutamic acid, the proteinogenic enantiomer, gives l-isoglutamine, which has S configuration. d-Isoglutamine, the derivative of the nonproteinogenic d-glutamic acid, has R configuration.^[2] The latter is the form occurring in MDP and mifamurtide.

References

↑ Drugs.com: Isoglutamine
↑ Brundish, D. E.; Wade, R. (1985). "Synthesis of N-[2-3H]acetyl-D-muramyl-L-alanyl-D-iso-glutaminyl-L-alanyl-2-(1',2'-dipalmitoyl-sn-glycero-3'-phosphoryl)ethylamide of high specific radioactivity". J Label Compd Radiopharm. 22 (1): 29–35. doi:10.1002/jlcr.2580220105.

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[1] Drugs.com: Isoglutamine

[2] Brundish, D. E.; Wade, R. (1985). "Synthesis of N-[2-3H]acetyl-D-muramyl-L-alanyl-D-iso-glutaminyl-L-alanyl-2-(1',2'-dipalmitoyl-sn-glycero-3'-phosphoryl)ethylamide of high specific radioactivity". J Label Compd Radiopharm. 22 (1): 29–35. doi:10.1002/jlcr.2580220105.

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