3-Hydroxyaspartic acid
(Redirected from C4H7NO5)
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| 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 | |
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| 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.
Structure
[edit]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]
Function
[edit]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
[edit]References
[edit]- ↑ 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. hdl:2115/62880. ISSN 0175-7598.
- ↑ 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.
- ↑ 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.