3-Hydroxyaspartic acid

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
3-Hydroxyaspartic acid
L-threo-3-Hydroxyaspartate
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
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 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
  • 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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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

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

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