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.
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IUPAC name
α-Glutamine
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Systematic IUPAC name
4,5-Diamino-5-oxopentanoic acid | |
Identifiers | |
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3D model (JSmol)
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Abbreviations | IsoGln |
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DrugBank |
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KEGG |
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PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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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).
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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
editSubstituting 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
edit- ^ "Drugs.com: Isoglutamine". Archived from the original on 2018-09-20. Retrieved 2018-01-23.
- ^ 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.