Isoglutamine

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

Names
IUPAC name 4,5-diamino-5-oxopentanoic acid
Identifiers
3D model (JSmol)	Interactive image
Abbreviations	IsoGln
ChemSpider	144380^Y
PubChem CID	164697 445883 (S/L) 5288447 (R/D)
InChI InChI=1S/C5H10N2O3/c6-3(5(7)10)1-2-4(8)9/h3H,1-2,6H2,(H2,7,10)(H,8,9)^Y Key: AEFLONBTGZFSGQ-UHFFFAOYSA-N^Y 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
SMILES O=C(N)C(N)CCC(=O)O
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).
Y verify (what is ^YN ?)
Infobox references

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

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.