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]

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).

Structure

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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

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

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

References

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  1. ^ Johnson, Brooke A.; Clark, Kenzie A.; Bushin, Leah B.; Spolar, Calvin N.; Seyedsayamdost, Mohammad R. (2024). "Expanding the Landscape of Noncanonical Amino Acids in RiPP Biosynthesis". Journal of the American Chemical Society. 146 (6): 3805–3815. doi:10.1021/jacs.3c10824. PMID 38316431.
  2. ^ Carter, Herbert E.; West, Harold D. (1940). "dl-Threonine". Organic Syntheses. 20: 101. doi:10.15227/orgsyn.020.0101.
  3. ^ Bonner, DP; O'Sullivan, J; Tanaka, SK; Clark, JM; Whitney, RR (1988). "Lysobactin, a Novel Antibacterial Agent Produced by Lysobacter sp. II. Biological Properties". The Journal of Antibiotics. 41 (12): 1745–51. doi:10.7164/antibiotics.41.1745. PMID 3209466.
  4. ^ Sarabia, Francisco; Chammaa, Samy; García-Ruiz, Cristina (2011). "Solid Phase Synthesis of Globomycin and SF-1902 A5". The Journal of Organic Chemistry. 76 (7): 2132–2144. doi:10.1021/jo1025145. PMID 21366318.