3-Hydroxyaspartic acid

3-Hydroxyaspartic acid
L-threo-3-Hydroxyaspartate
Names
Preferred IUPAC name
(2S)-2-Amino-3-hydroxybutanedioic acid
Other names
(2S)-2-Amino-3-hydroxysuccinic acid
3-Hydroxyaspartic acid
Beta-hydroxyaspartic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
InChI
  • InChI=1S/C4H7NO5/c5-1(3(7)8)2(6)4(9)10/h1-2,6H,5H2,(H,7,8)(H,9,10)/t1-,2-/m0/s1 checkY
    Key: YYLQUHNPNCGKJQ-LWMBPPNESA-N checkY
  • InChI=1/C4H7NO5/c5-1(3(7)8)2(6)4(9)10/h1-2,6H,5H2,(H,7,8)(H,9,10)/t1-,2-/m0/s1
    Key: YYLQUHNPNCGKJQ-LWMBPPNEBT
SMILES
  • C(C(C(=O)O)O)(C(=O)O)N
  • O=C(O)[C@@H](N)[C@H](O)C(=O)O
Properties
Chemical formula
 C4H7NO5
Molar mass 149.102 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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Infobox references

3-Hydroxyaspartic acid (three letter abbreviation: Hya) also known as beta-hydroxyaspartic acid is derivative of aspartic acid which has been hydroxylated at position-3. The adjacent image shows L-threo-3-Hydroxyaspartate. The conjugated acid of 3-hydroxyaspartic acid is 3-hydroxyaspartate.

Structure

Similarly to proteinogenic isoleucine and threonine, 3-hydroxyaspartic acid contains two chiral centers. As such, it can exist in 4 stereoisomers, which form two pairs of enantiomers.

Function

The Hya amino acid residue is sometimes contained in EGF-like domains such as Vitamin K-dependent coagulation plasma proteins including protein C.[1]

D-threo-3-Hydroxyaspartate is a part of the siderophore ornibactin.[2]

See also

  • Epidermal growth factor (EGF)
  • Vitamin K-dependent protein

References

  1. ↑ Castellino FJ, Ploplis VA, Zhang L (2008). "Γ-Glutamate and β–Hydroxyaspartate in Proteins". gamma-Glutamate and beta-hydroxyaspartate in proteins. Methods Mol. Biol. Vol. 446. pp. 85–94. doi:10.1007/978-1-60327-084-7_6. ISBN 978-1-58829-719-8. PMID 18373251.
  2. ↑ Stephan, Holger; Freund, Stefan; Beck, Werner; Jung, Günther; Meyer, Jean-Marie; Winkelmann, Günther (1993-06-01). "Ornibactins—a new family of siderophores from Pseudomonas". Biometals. 6 (2): 93–100. doi:10.1007/BF00140109. ISSN 1572-8773.


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