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
(S/L)-Isoglutamine
(R/D)-Isoglutamine
Names
IUPAC name
α-Glutamine
Systematic IUPAC name
4,5-Diamino-5-oxopentanoic acid
Identifiers
3D model (JSmol)
Abbreviations IsoGln
ChemSpider
DrugBank
KEGG
UNII
  • InChI=1S/C5H10N2O3/c6-3(5(7)10)1-2-4(8)9/h3H,1-2,6H2,(H2,7,10)(H,8,9) checkY
    Key: AEFLONBTGZFSGQ-UHFFFAOYSA-N checkY
  • 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
  • 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
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).
checkY verify (what is checkY☒N ?)
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". Archived from the original on 2018-09-20. Retrieved 2018-01-23.
  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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