isoglutamine

{{chembox

| verifiedrevid = 443890865

| ImageFile1 = S-Isoglutamine skeletal.svg

| ImageName1 = (S/L)-Isoglutamine

| ImageFile2 = R-Isoglutamine skeletal.svg

| 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 = {{cascite|correct|CAS}}

| CASNo = 328-48-3

| CASNo2_Ref = {{cascite|correct|CAS}}

| CASNo2 = 636-65-7

| CASNo3_Ref = {{cascite|correct|CAS}}

| 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 = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 144380

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| 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 = {{stdinchicite|correct|chemspider}}

| 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@@H](C(=O)N)N

| SMILES3 = C(CC(=O)O)[C@H](C(=O)N)N

}}

| 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.{{Cite web |url=https://www.drugs.com/dict/isoglutamine.html |title=Drugs.com: Isoglutamine |access-date=2018-01-23 |archive-date=2018-09-20 |archive-url=https://web.archive.org/web/20180920172543/https://www.drugs.com/dict/isoglutamine.html |url-status=dead }} 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.