MetaCyc Enzyme: 4-fluorothreonine transaldolase

Gene: 4-FTase Accession Number: G-12241 (MetaCyc)

Species: Streptomyces cattleya

Subunit composition of 4-fluorothreonine transaldolase = [4-FTase]2
         4-fluorothreonine transaldolase monomer = 4-FTase

Radio-isotopic studies have suggested that 4-fluorothreonine was produced from fluoroacetaldehyde in the bacterium Streptomyces cattleya, although the exact mechanism was not known [Sanada86, Reid95, Moss00].

A subsequent study has revealed that incubation of cell-free extracts of Streptomyces cattleya with L-threonine, pyridoxal 5'-phosphate (PLP), and fluoroacetaldehyde results in the formation of 4-fluorothreonine [Murphy01]. The enzyme responsible for this reaction, 4-fluorothreonine transaldolase, was purified and characterized. The enzyme forms a homodimer in solution [Murphy01].

The gene encoding the enzyme was identified by a complex process [Deng08]. Partial amino acid sequences obtained by sequencing fragments of the purified protein were used for PCR ampliofication of a fragment of the genome. Chromosome walking identified the full gene. The gene was cloned and overexpressed in Streptomyces lividans. Even though the expression level was low, cell extracts prepared from the transformed host were able to catalyze the conversion of L-threonine and fluoroacetaldehyde to 4-fluorothreonine. The enzyme was partially purified [Deng08].

Molecular Weight of Polypeptide: 69.529 kD (from nucleotide sequence), 60.0 kD (experimental) [Murphy01 ]

Unification Links: Entrez-Nucleotide:FM251921 , Protein Model Portal:B6VP39 , UniProt:B6VP39

Relationship Links: InterPro:IN-FAMILY:IPR001085 , InterPro:IN-FAMILY:IPR001303 , InterPro:IN-FAMILY:IPR015421 , InterPro:IN-FAMILY:IPR015422 , InterPro:IN-FAMILY:IPR015424 , Panther:IN-FAMILY:PTHR11680 , Pfam:IN-FAMILY:PF00464 , Pfam:IN-FAMILY:PF00596 , Smart:IN-FAMILY:SM01007

Gene-Reaction Schematic: ?

Gene-Reaction Schematic

Created 06-Oct-2010 by Caspi R , SRI International
Revised 07-Oct-2010 by Caspi R , SRI International

Enzymatic reaction of: 4-fluorothreonine transaldolase

EC Number:

fluoroacetaldehyde + L-threonine <=> acetaldehyde + 4-fluorothreonine

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is favored in the direction shown.

Alternative Products for 4-fluorothreonine: chloroacetaldehyde [Murphy01 ]

In Pathways: fluoroacetate and fluorothreonine biosynthesis

Cofactors or Prosthetic Groups: pyridoxal 5'-phosphate [Murphy01]


Deng08: Deng H, Cross SM, McGlinchey RP, Hamilton JT, O'Hagan D (2008). "In vitro reconstituted biotransformation of 4-fluorothreonine from fluoride ion: application of the fluorinase." Chem Biol 15(12);1268-76. PMID: 19101471

Moss00: Moss, S.J., Murphy, C.D., Hamilton, J.T.G., McRobert, W.C., O'Hagan, D., Schaffrath, C., Harper, D.B. (2000). "Fluoroacetaldehyde: A precursor of both fluoroacetate and 4-fluorothreonine in Streptomyces cattleya." Chemical Communications 22:2281-2282.

Murphy01: 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. PMID: 12404452

Reid95: Reid KA, Hamilton JT, Bowden RD, O'Hagan D, Dasaradhi L, Amin MR, Harper DB (1995). "Biosynthesis of fluorinated secondary metabolites by Streptomyces cattleya." Microbiology 141 ( Pt 6);1385-93. PMID: 7670640

Sanada86: Sanada M, Miyano T, Iwadare S, Williamson JM, Arison BH, Smith JL, Douglas AW, Liesch JM, Inamine E (1986). "Biosynthesis of fluorothreonine and fluoroacetic acid by the thienamycin producer, Streptomyces cattleya." J Antibiot (Tokyo) 39(2);259-65. PMID: 3082840

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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