Isoglutamine

Isoglutamine

Isoglutamine

Chemical compound

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.

Quick Facts Names, Identifiers ...

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. [1]
    "Drugs.com: Isoglutamine". Archived from the original on 2018-09-20. Retrieved 2018-01-23.
  2. [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.
Share this article:

This article uses material from the Wikipedia article Isoglutamine, and is written by contributors. Text is available under a CC BY-SA 4.0 International License; additional terms may apply. Images, videos and audio are available under their respective licenses.