4-Fluoro-L-threonine

Last updated
4-Fluoro-l-threonine
4-Fluorothreonine.svg
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
PubChem CID
  • 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]

Related Research Articles

<i>Cattleya</i> Genus of orchids

Cattleya is a genus of orchids from Costa Rica south to Argentina. The genus is abbreviated C in trade journals.

Antimycins are produced as secondary metabolites by Streptomyces bacteria, a soil bacteria. These specialized metabolites likely function to kill neighboring organisms in order to provide the streptomyces bacteria with a competitive edge.

<span class="mw-page-title-main">Lactacystin</span> Chemical compound

Lactacystin is an organic compound naturally synthesized by bacteria of the genus Streptomyces first identified as an inducer of neuritogenesis in neuroblastoma cells in 1991. The target of lactacystin was subsequently found to be the proteasome on the basis of its affinity for certain catalytic subunits of the proteasome by Fenteany and co-workers in 1995. The proteasome is a protein complex responsible for the bulk of proteolysis in the cell, as well as proteolytic activation of certain protein substrates. Lactacystin was the first non-peptidic proteasome inhibitor discovered and is widely used as a research tool in biochemistry and cell biology. The transformation product of lactacystin clasto-lactacystin β-lactone covalently modifies the amino-terminal threonine of specific catalytic subunits of the proteasome, a discovery that helped to establish the proteasome as a mechanistically novel class of protease: an amino-terminal threonine protease. The molecule is commonly used in biochemistry and cell biology laboratories as a selective inhibitor of the proteasome. The first total synthesis of lactacystin was developed in 1992 by Corey and Reichard, and a number of other syntheses of this molecule have also been published. There are more than 1,660 entries for lactacystin in PubMed as of January 2019.

<span class="mw-page-title-main">Transaldolase</span> Enzyme family

Transaldolase is an enzyme of the non-oxidative phase of the pentose phosphate pathway. In humans, transaldolase is encoded by the TALDO1 gene.

<span class="mw-page-title-main">Thienamycin</span> Chemical compound

Thienamycin is one of the most potent naturally produced antibiotics known thus far, discovered in Streptomyces cattleya in 1976. Thienamycin has excellent activity against both Gram-positive and Gram-negative bacteria and is resistant to bacterial β-lactamase enzymes. Thienamycin is a zwitterion at pH 7.

In enzymology, a fluoroacetaldehyde dehydrogenase (EC 1.2.1.69) is an enzyme that catalyzes the chemical reaction

In enzymology, a 1-deoxy-d-xylulose-5-phosphate synthase (EC 2.2.1.7) is an enzyme in the non-mevalonate pathway that catalyzes the chemical reaction

In enzymology, a fluorothreonine transaldolase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Fluorinase</span>

The fluorinase enzyme catalyzes the reaction between fluoride ion and the co-factor S-adenosyl-L-methionine to generate L-methionine and 5'-fluoro-5'-deoxyadenosine, the first committed product of the fluorometabolite biosynthesis pathway. The fluorinase was originally isolated from the soil bacterium Streptomyces cattleya, but homologues have since been identified in a number of other bacterial species, including Streptomyces sp. MA37, Nocardia brasiliensis and Actinoplanes sp. N902-109. This is the only known enzyme capable of catalysing the formation of a carbon-fluorine bond, the strongest single bond in organic chemistry.

<span class="mw-page-title-main">Transaldolase deficiency</span> Medical condition

Transaldolase deficiency is a disease characterised by abnormally low levels of the transaldolase enzyme. It is a metabolic enzyme involved in the pentose phosphate pathway. It is caused by mutation in the transaldolase gene (TALDO1). It was first described by Verhoeven et al. in 2001.

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Streptomyces cattleya is a Gram-positive bacterium which makes cephamycin, penicillin and thienamycin. The bacterium expresses a fluorinase enzyme, and the organism has been used to understand the biosynthesis of fluoroacetate and the antibacterial 4-fluoro-L-threonine. The γ-Glu-βes pathway to biosynthesis of non-traditional amino acids β-ethynylserine (βes) and L-propargylglycine (Pra) was first characterized in this species.

<span class="mw-page-title-main">Fluoroacetaldehyde</span> Chemical compound

Fluoroacetaldehyde is a metabolic precursor of both fluoroacetate and 4-fluorothreonine in Streptomyces cattleya.

<span class="mw-page-title-main">Cyclothiazomycin</span> Chemical compound

The cyclothiazomycins are a group of natural products, classified as thiopeptides, which are produced by various Streptomyces species of bacteria.

Streptomyces iakyrus is a bacterium species from the genus of Streptomyces which has been isolated from soil Streptomyces iakyrus produces actinomycin G2, actinomycin G3, actinomycin G4, actinomycin G5, actinomycin G6, iakirine I, iakirine II and iakirine III.

Streptomyces nojiriensis is a bacterium species from the genus of Streptomyces which has been isolated from soil from the Lake Nojiri in Japan. Streptomyces nojiriensis produces nojirimycin.

Streptomyces subrutilus is a bacterium species from the genus of Streptomyces. Streptomyces subrutilus produces deoxynojirimycin, deoxymannonojirimycin and hydroxystreptomycin.

<span class="mw-page-title-main">Nucleocidin</span> Chemical compound

Nucleocidin is a fluorine-containing nucleoside produced by Streptomyces calvus.

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.