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L-threo-3-Methylaspartate

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l-threo-3-Methylaspartate
L-threo-3-methylaspartate
Names
IUPAC name (3S)-3-Methyl-L-aspartic acid
Systematic IUPAC name (2S,3S)-2-Amino-3-methylbutanedioic acid
Other names l-threo-3-Methylaspartate; 3-Methylaspartic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: 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/s1Key: LXRUAYBIUSUULX-HRFVKAFMBX
SMILES
  • C((C(=O)O)N)C(=O)O
Properties
Chemical formula C5H9NO4
Molar mass 147.130 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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 and vicenistatin and in carbon metabolism of haloarchaea (Methylaspartate cycle).

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. Bibcode:2011Sci...331..334K. doi:10.1126/science.1196544. PMID 21252347. S2CID 206529403.
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