|PubChem||, (S/L), (R/D)|
|Jmol-3D images||Image 1|
|Molar mass||146.14 g mol−1|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
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. 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.
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. The latter is the form occurring in MDP and mifamurtide.