Isoglutamine

Isoglutamine
IUPAC name 4,5-diamino-5-oxopentanoic acid
Identifiers
Abbreviations	IsoGln
	PubChem	164697, 445883 (S/L), 5288447 (R/D)
ChemSpider	144380 Y
Jmol-3D images	Image 1
SMILES O=C(N)C(N)CCC(=O)O
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
Properties
Molecular formula	C5H10N2O3
Molar mass	146.14 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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