3-Hydroxyaspartic acid

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3-Hydroxyaspartic acid
L-threo-3-Hydroxyaspartate 3-hydroxyaspartic acid.svg
L-threo-3-Hydroxyaspartate
Names
Preferred IUPAC name
(2S, 3Ξ)-2-Amino-3-hydroxybutanedioic acid
Other names
(2S, 3Ξ)-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).
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3-Hydroxyaspartic acid (three letter abbreviation: Hya), also known as beta-hydroxyaspartic acid, is a derivative of aspartic acid which has been hydroxylated at position C3. The conjugated acid of 3-hydroxyaspartic acid is 3-hydroxyaspartate. The adjacent image shows L-threo-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. [1]

Isomers of 3-hydroxyaspartate 3-hydroxyaspartate isomers.svg
Isomers of 3-hydroxyaspartate

Function

The Hya amino acid residue is sometimes contained in EGF-like domains such as Vitamin K-dependent coagulation plasma proteins including protein C. [2]

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

See also

References

  1. ↑ Matsumoto, Yu; Yasutake, Yoshiaki; Takeda, Yuki; Tamura, Tomohiro; Yokota, Atsushi; Wada, Masaru (September 2015). "Structural insights into the substrate stereospecificity of d-threo-3-hydroxyaspartate dehydratase from Delftia sp. HT23: a useful enzyme for the synthesis of optically pure l-threo- and d-erythro-3-hydroxyaspartate". Applied Microbiology and Biotechnology. 99 (17): 7137–7150. doi:10.1007/s00253-015-6479-3. ISSN   0175-7598.
  2. ↑ 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.
  3. ↑ 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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