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Chemical Compound Review:

Pardinon 2-amino-3-(3-fluoro-4- hydroxy...

Synonyms: Fluorthyrin, m-Ftyr, SureCN274650, Bio-0619, ACMC-1B2C7, ...

Ayala, I. et al., Hazard, E.S. et al., Quint, P. et al., Dupureur, C.M. et al., Lu, P. et al., et al.

Dupureur, Hallman,

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Disease relevance of m-Ftyr

Conditions are described that can be used for the 3-fluorotyrosine substitution of a variety of Escherichia coli proteins for 19F nuclear magnetic resonance studies [1].

High impact information on m-Ftyr

By using a systematic genetic approach, the resonances in the 19F NMR spectrum of 3-fluorotyrosine-substituted lac repressor protein have been assigned [2].
Free Tyr was iodinated at the same rate as Tyr peptides by lactoperoxidase, but monoiodotyrosine and m-fluorotyrosine were iodinated at one-half that rate [3].
The 19F NMR spectrum of this enzyme showed five sharp resonances that have been assigned by site-specific mutagenesis by replacing each 3-fluorotyrosine with phenylalanine; four 19F resonances not observed are near the paramagnetic manganese and extensively broadened [4].
Incorporation of 3-fluorotyrosine and site-specific mutagenesis has been utilized with Fourier transform infrared (FTIR) spectroscopy and x-ray crystallography to elucidate active-site structure and the role of an active-site residue Tyr34 in human manganese superoxide dismutase (MnSOD) [5].
19F-n.m.r. studies of ligand binding to 5-fluorotryptophan- and 3-fluorotyrosine-containing cyclic AMP receptor protein from Escherichia coli [6].

Anatomical context of m-Ftyr

Halobacterium halobium, grown in a defined medium where tyrosine had been largely replaced with m-fluorotyrosine, biosynthetically produced purple membrane [7].

Associations of m-Ftyr with other chemical compounds

Hydrogen bonding in human manganese superoxide dismutase containing 3-fluorotyrosine [5].
Analysis of this membrane by high pressure liquid chromatography of phenylthiocarbamyl derivatized amino acids of membrane acid hydrolysates revealed that up to 50% of the tyrosine was present as the m-fluorotyrosine form [7].

Gene context of m-Ftyr

Replacement of 74% (+/- 10%) of the Tyr residues in PvuII endonuclease by 3-fluorotyrosine produces an enzyme with Mg(II)-supported specific activity and sequence specificity that is indistinguishable from that of the native enzyme [8].
The pH profiles of beta-galactosidase, having tyr replaced by m-fluorotyrosine, were compared to those of normal enzyme [9].
An analogue of elongation factor Tu (EF-Tu) from Escherichia coli was prepared by biosynthetic incorporation of 3-fluorotyrosine [10].
Of several tyrosine derivatives tested, only m-fluorotyrosine supported the growth of this mutant and allowed synthesis of active beta-galactosidase [11].

Analytical, diagnostic and therapeutic context of m-Ftyr

The FTIR data show distinct vibrational modes arising from 3-fluorotyrosine in MnSOD [5].

References

lac repressor: 3-fluorotyrosine substitution for nuclear magnetic resonance studies. Lu, P., Jarema, M., Mosser, K., Daniel, W.E. Proc. Natl. Acad. Sci. U.S.A. (1976) [Pubmed]
Genetic assignment of resonances in the NMR spectrum of a protein: lac repressor. Jarema, M.A., Lu, P., Miller, J.H. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
Studies on the mechanism of the iodination of tyrosine by lactoperoxidase. Huber, R.E., Edwards, L.A., Carne, T.J. J. Biol. Chem. (1989) [Pubmed]
Structural mobility in human manganese superoxide dismutase. Quint, P., Ayala, I., Busby, S.A., Chalmers, M.J., Griffin, P.R., Rocca, J., Nick, H.S., Silverman, D.N. Biochemistry (2006) [Pubmed]
Hydrogen bonding in human manganese superoxide dismutase containing 3-fluorotyrosine. Ayala, I., Perry, J.J., Szczepanski, J., Tainer, J.A., Vala, M.T., Nick, H.S., Silverman, D.N. Biophys. J. (2005) [Pubmed]
19F-n.m.r. studies of ligand binding to 5-fluorotryptophan- and 3-fluorotyrosine-containing cyclic AMP receptor protein from Escherichia coli. Sixl, F., King, R.W., Bracken, M., Feeney, J. Biochem. J. (1990) [Pubmed]
Biosynthetic incorporation of m-fluorotyrosine into bacteriorhodopsin. Hazard, E.S., Govindjee, R., Ebrey, T.G., Crouch, R.K. Photochem. Photobiol. (1992) [Pubmed]
Effects of divalent metal ions on the activity and conformation of native and 3-fluorotyrosine-PvuII endonucleases. Dupureur, C.M., Hallman, L.M. Eur. J. Biochem. (1999) [Pubmed]
m-Fluorotyrosine substitution in beta-galactosidase; evidence for the existence of a catalytically active tyrosine. Ring, M., Armitage, I.M., Huber, R.E. Biochem. Biophys. Res. Commun. (1985) [Pubmed]
Conformational differences between complexes of elongation factor Tu studied 19F-NMR spectroscopy. Eccleston, J.F., Molloy, D.P., Hinds, M.G., King, R.W., Feeney, J. Eur. J. Biochem. (1993) [Pubmed]
The properties of beta-galactosidases (Escherichia coli) with halogenated tyrosines. Ring, M., Huber, R.E. Biochem. Cell Biol. (1993) [Pubmed]

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