4-Fluoro-L-threonine

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4-Fluoro-l-threonine
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 antibacterial produced by Streptomyces cattleya. It is formed by the fluorothreonine transaldolase catalysed transfer of fluoroacetaldehyde onto threonine.[1]

References

  1. ^ 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 This work was supported by the Biotechnological and Biological Sciences Research Council and the University of St Andrews". 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.
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