Article · Wikipedia archive · Last revised Jul 17, 2026

4-Fluoro-L-threonine

4-Fluoro-l-threonine is an antibiotic produced by Streptomyces cattleya.

Last revised
Jul 17, 2026
Read time
≈ 1 min
Length
241 w
Citations
4
Source
Wikipedia ↗
4-Fluoro-l-threonine
source ↗
Names
IUPAC name
4-Fluoro-L-threonine
Systematic IUPAC name
(2S,3S)-2-Amino-4-fluoro-3-hydroxybutanoic acid
Other names
4-Fluorothreonine
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C4H8FNO3/c5-1-2(7)3(6)4(8)9/h2-3,7H,1,6H2,(H,8,9)/t2-,3+/m1/s1
    Key: GTFWIYJIEXNAOL-GBXIJSLDSA-N
  • InChI=1/C4H8FNO3/c5-1-2(7)3(6)4(8)9/h2-3,7H,1,6H2,(H,8,9)/t2-,3+/m1/s1
    Key: GTFWIYJIEXNAOL-GBXIJSLDBB
  • C([C@H]([C@@H](C(=O)O)N)O)F
Properties
C4H8FNO3
Molar mass 137.110 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4-Fluoro-l-threonine is an antibiotic produced by Streptomyces cattleya.12

Biosynthesis

The enzyme fluorothreonine transaldolase catalyzes the chemical reaction which converts the natural amino acid threonine to 4-fluoro-L-threonine in the Streptomyces cattleya.34

2D representation of the chemical structure of Threonine.
L-threonine
+
 
2D representation of the chemical structure of fluoroacetaldehyde.
Fluoro­acetaldehyde
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of 4-Fluoro-L-threonine.
4-Fluoro-L-threonine
+
 
2D representation of the chemical structure of Acetaldehyde .
Acetaldehyde


References

References

  1. Sanada, Minoru; Miyano, Tetsuji; Iwadare, Shuichi; Williamson, Joanne M.; Arison, Byron H.; Smith, Jack L.; Douglas, Alan W.; Liesch, Jerrold M.; Inamine, Edward (1986). "Biosynthesis of fluorothreonine and fluoroacetic acid by the thienamycin producer, Streptomyces cattleya". The Journal of Antibiotics. 39 (2): 259–265. doi:10.7164/antibiotics.39.259. PMID 3082840.
  2. Chandra, Girish; Mahato, Gopal Kumar; Mahto, Birkishore (2024). "Biosynthesis and Synthetic Biology of Fluorinated Products in Plants". Biosynthesis of Natural Products in Plants. pp. 381–403. doi:10.1007/978-981-97-2166-5_16. ISBN 978-981-97-2165-8.
  3. Murphy CD, O'Hagan D, Schaffrath C (2001). "Identification of a PLP-Dependent Threonine Transaldolase: A Novel Enzyme Involved in 4-Fluorothreonine Biosynthesis in Streptomyces cattleya". Angew. Chem. Int. Ed. Engl. 40 (23): 4479–4481. doi:10.1002/1521-3773(20011203)40:23<4479::AID-ANIE4479>3.0.CO;2-1. PMID 12404452.
  4. Murphy CD, Schaffrath C, O'Hagan D (2003). "Fluorinated natural products: the biosynthesis of fluoroacetate and 4-fluorothreonine in Streptomyces cattleya". Chemosphere. 52 (2): 455–61. Bibcode:2003Chmsp..52..455M. doi:10.1016/S0045-6535(03)00191-7. PMID 12738270.