Allothreonine

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
Allothreonine
L-Allothreonine
D-Allothreonine
Names
Other names
(2S,3S)-2-amino-3-hydroxybutanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • L-: 249-327-2
KEGG
UNII
  • InChI=1/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3-/s2
    Key: AYFVYJQAPQTCCC-HSGWWGIINA-N
  • L-: InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3-/m0/s1
    Key: AYFVYJQAPQTCCC-HRFVKAFMSA-N
  • DL-: CC(C(C(=O)O)N)O
  • L-: C[C@@H]([C@@H](C(=O)O)N)O
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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Structure

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.

 
L-Threonine (2S,3R) and D-Threonine (2R,3S)
 
L-Allothreonine (2S,3S) and D-Allothreonine (2R,3R)

Occurrence

Katanosins are a group of potent antibiotics containing allothreonine.[3]

Peptides containing the allothreonine residue have also been isolated from natural sources.[4]

References

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