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Names | |||
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Other names
(2S,3S)-2-amino-3-hydroxybutanoic acid
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Identifiers | |||
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3D model (JSmol)
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ChEBI |
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ChEMBL |
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ChemSpider | |||
EC Number |
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KEGG |
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PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |||
C4H9NO3 | |||
Molar mass | 119.120 g·mol−1 | ||
Appearance | White solid | ||
Melting point | 273.5–275.0 °C (524.3–527.0 °F; 546.6–548.1 K) decomposition | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Allothreonine is an amino acid with the formula CH3CH(OH)CH(NH2)CO2H. It is the diastereomer of the amino acid threonine. Like most other amino acids, allothreonine is a water-soluble colorless solid. Although not one of the proteinogenic amino acids, it has often been the subject for the synthesis of novel proteins using an expanded genetic code.[1] Racemic allothreonine can be produced in the laboratory from bromomethoxybutyric acid.[2]
Threonine has R, S stereochemistry at carbons 2 and 3 for the naturally occurring stereoisomer and S, R stereochemistry for its enantiomer. Allothreonine has S, S stereochemistry at carbons 2 and 3 in the natural stereoisomer, but R, R in the very rare enantiomer.
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L-Threonine (2S,3R) and D-Threonine (2R,3S) |
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L-Allothreonine (2S,3S) and D-Allothreonine (2R,3R) |
Katanosins are a group of potent antibiotics contain allothreonine.[3]
Peptides containing the allothreonine residue have also been isolated from natural source.[4]