3-Hydroxyaspartic acid

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3-Hydroxyaspartic acid
3-hydroxyaspartic acid.svg
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
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: YYLQUHNPNCGKJQ-LWMBPPNESA-N Yes check.svgY
  • 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
  • C(C(C(=O)O)O)(C(=O)O)N
  • O=C(O)[C@@H](N)[C@H](O)C(=O)O
Properties
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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

Related Research Articles

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threo-3-Hydroxy-D-aspartate ammonia-lyase (EC 4.3.1.27, D-threo-3-hydroxyaspartate dehydratase) is an enzyme with systematic name threo-3-hydroxy-D-aspartate ammonia-lyase (oxaloacetate-forming). This enzyme catalyses the following chemical reaction

Ornibactin is a siderophore, or small iron-binding compound secreted by bacteria to transport iron into the cell. Ornibactin is produced by Burkholderia cenocepacia under iron-deficient conditions. B. cenocepacia is known to opportunistically infect humans, specifically ones suffering from cystic fibrosis.

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.