Isoglutamine

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Isoglutamine
(S/L)-Isoglutamine
(R/D)-Isoglutamine
Identifiers
Abbreviations IsoGln
PubChem 164697, 445883 (S/L), 5288447 (R/D)
ChemSpider 144380 YesY
Jmol-3D images Image 1
Properties
Molecular formula C5H10N2O3
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)
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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[edit]

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[edit]

  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.