Isoglutamine

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title: "Isoglutamine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["gamma-amino-acids"] topic_path: "general/gamma-amino-acids" source: "https://en.wikipedia.org/wiki/Isoglutamine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| verifiedrevid = 443890865 | ImageFile1 = S-Isoglutamine skeletal.svg | ImageClass1 = skin-invert-image | ImageName1 = (S/L)-Isoglutamine | ImageFile2 = R-Isoglutamine skeletal.svg | ImageClass2 = skin-invert-image | ImageName2 = (R/D)-Isoglutamine | IUPACName = α-Glutamine | OtherNames = | SystematicName = 4,5-Diamino-5-oxopentanoic acid | Section1 = {{Chembox Identifiers | Abbreviations = IsoGln | index_label=DL | index2_label=(S/L) | index3_label=(R/D) | InChI1 = 1/C5H10N2O3/c6-3(5(7)10)1-2-4(8)9/h3H,1-2,6H2,(H2,7,10)(H,8,9) | InChIKey1 = AEFLONBTGZFSGQ-UHFFFAOYAS | CASNo_Ref = | CASNo = 328-48-3 | CASNo2_Ref = | CASNo2 = 636-65-7 | CASNo3_Ref = | CASNo3 = 19522-40-8 | DrugBank2 = DB03091 | DTXSID3 = DTXSID90415341 | KEGG = C16673 | PubChem = 164697 | PubChem2 = 445883 | PubChem3 = 5288447 | UNII = 00VZE9Y4WF | UNII2 = WL74QNU57B | UNII3 = IY2O406N69 | InChI= 1S/C5H10N2O3/c6-3(5(7)10)1-2-4(8)9/h3H,1-2,6H2,(H2,7,10)(H,8,9) | ChemSpiderID_Ref = | ChemSpiderID = 144380 | StdInChI_Ref = | StdInChI = 1S/C5H10N2O3/c6-3(5(7)10)1-2-4(8)9/h3H,1-2,6H2,(H2,7,10)(H,8,9) | StdInChIKey_Ref = | StdInChIKey = AEFLONBTGZFSGQ-UHFFFAOYSA-N | InChI2=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 | InChIKey2 = AEFLONBTGZFSGQ-VKHMYHEASA-N | InChI3=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 | InChIKey3 = AEFLONBTGZFSGQ-GSVOUGTGSA-N | SMILES = O=C(N)C(N)CCC(=O)O | SMILES2 = C(CC(=O)O)C@@HN | SMILES3 = C(CC(=O)O)C@HN | Section2 = {{Chembox Properties | Properties_ref = | C=5 | H=10 | N=2 | O=3 | Appearance = | Density = | MeltingPt = | Solubility = | SpecRotation =

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 -glutamic acid, the proteinogenic enantiomer, gives -isoglutamine, which has S configuration. -Isoglutamine, the derivative of the nonproteinogenic -glutamic acid, has R configuration. The latter is the form occurring in muramyl dipeptide and mifamurtide.

References

References

  1. "Drugs.com: Isoglutamine".
  2. (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.

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gamma-amino-acids