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

^ 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.
^ Carter, Herbert E.; West, Harold D. (1940). "dl-Threonine". Organic Syntheses. 20: 101. doi:10.15227/orgsyn.020.0101.
^ 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.
^ 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.

[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.

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