L-threo-3-Methylaspartate

L-threo-3-Methylaspartate

Names
IUPAC name (2S,3S)-2-Amino-3-methylbutanedioic acid
Other names L-threo-3-Methylaspartate; 3-Methylaspartic acid
Identifiers
CAS Number	6061-13-8
3D model (Jmol)	Interactive image
ChEBI	CHEBI:47980
ChemSpider	389071
KEGG	C03618
PubChem	440064
InChI InChI=1S/C5H9NO4/c1-2(4(7)8)3(6)5(9)10/h2-3H,6H2,1H3,(H,7,8)(H,9,10)/t2-,3-/m0/s1 Key: LXRUAYBIUSUULX-HRFVKAFMSA-N InChI=1/C5H9NO4/c1-2(4(7)8)3(6)5(9)10/h2-3H,6H2,1H3,(H,7,8)(H,9,10)/t2-,3-/m0/s1 Key: LXRUAYBIUSUULX-HRFVKAFMBX
SMILES C[C@@H]([C@@H](C(=O)O)N)C(=O)O
Properties
Chemical formula	C5H9NO4
Molar mass	147.13 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

L-threo-3-Methylaspartate is an unusual amino acid formed by glutamate mutase and can be metabolised by methylaspartate ammonia-lyase. It is found in the structures of the antibiotics friulimicin^[1] and vicenistatin^[1] and in carbon metabolism of haloarchaea (Methylaspartate cycle).^[2]

References

1. Ogasawara, Y.; Kakinuma, K.; Eguchi, T. (2005). "Involvement of Glutamate Mutase in the Biosynthesis of the Unique Starter Unit of the Macrolactam Polyketide Antibiotic Vicenistatin". The Journal of Antibiotics. 58 (7): 468–72. doi:10.1038/ja.2005.62. PMID 16161486.
2. Khomyakova, M.; Bukmez, O.; Thomas, L. K.; Erb, T. J.; Berg, I. A. (2011). "A Methylaspartate Cycle in Haloarchaea". Science. 331 (6015): 334–7. doi:10.1126/science.1196544. PMID 21252347.