3-Hydroxyaspartic acid

3-Hydroxyaspartic acid

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	1860-87-3^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:10696^Y
ChemSpider	391503^Y
IUPHAR/BPS	4497
KEGG	C11511^Y
PubChem CID	443239
UNII	99A78V5YX2^Y
CompTox Dashboard (EPA)	DTXSID301017241
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^Y Key: YYLQUHNPNCGKJQ-LWMBPPNESA-N^Y 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). N verify (what is ^YN ?) 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.