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. 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. The latter is the form occurring in muramyl dipeptide and mifamurtide.
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Datasets, specimens, observations and peer-reviewed methods provide the appropriate test for the technical claims summarized here. The source revision retrieved here is dated Sep 14, 2026. The linked authority identifier is Q6085727. None of the 0 selected statements returned an explicit reference.
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This entry incorporates text from “Isoglutamine” on English Wikipedia. Contributors are listed in the page history. Text is available under the Creative Commons Attribution-ShareAlike 4.0 License. Selected authority identifiers and statements are retrieved from Wikidata under CC0; their references and qualifiers remain part of the verification path.