Allothreonine Explained

Allothreonine is an amino acid with the formula . 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]

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.

Occurrence

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

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

References

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