Allothreonine

Allothreonine

L-Allothreonine D-Allothreonine
Names
Other names (2S,3S)-2-amino-3-hydroxybutanoic acid
Identifiers
CAS Number	DL-: 144-98-9 L-: 28954-12-3
3D model (JSmol)	DL-: Interactive image L-: Interactive image
ChEBI	L-: CHEBI:28718
ChEMBL	L-: ChEMBL59238
ChemSpider	DL-: 200 L-: 89699
EC Number	L-:249-327-2
KEGG	L-: C05519
PubChem CID	L-: 99289
UNII	DL-: 29NAP6417F L-: HCQ253CKVK
CompTox Dashboard (EPA)	DL-: DTXSID301030659 L-: DTXSID10183151
InChI 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
SMILES DL-:CC(C(C(=O)O)N)O L-:C[C@@H]([C@@H](C(=O)O)N)O
Properties
Chemical formula	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). Infobox references

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]

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 contain allothreonine. ^[3]

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

References

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. Bibcode:2024JAChS.146.3805J. 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.