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Chemical Compound Review

TRIFLUOROACETATE     2,2,2-trifluoroethanoate

Synonyms: AG-D-88126, CHEBI:27110, CF3CO2 anion, ZINC03860798, AR-1L7362, ...
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Disease relevance of TRIFLUOROACETATE

 

High impact information on TRIFLUOROACETATE

  • Transport and fate of trifluoroacetate in upland forest and wetland ecosystems [4].
  • We now report the design and synthesis of a small molecule (M(r) 810, as its trifluoroacetate salt), water soluble, proteolytically stable mimetic of residues Gln40-Thr45 of the complementarity-determining 2-like region of CD4 [5].
  • A direct rate assay for plasminogen activator has been developed using a synthetic fluorogenic peptide substrate, 7-(N-Cbz-glycylglycylargininamido)-4-methylcoumarin trifluoroacetate [6].
  • The distribution, dynamics, and local environments of the TFA-modified titania, PEO, and PPO components of the hybrid were investigated [7].
  • The leaving group of the allylic esters affects the reaction considerably: allylic trifluoroacetate gave the best result, while the corresponding acetates and trichloroacetates did not afford any acylation products at all [8].
 

Chemical compound and disease context of TRIFLUOROACETATE

 

Biological context of TRIFLUOROACETATE

  • 5-(3-Methyl-1,2,4-oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidine+ ++ trifluoroacetate (CDD-0098-J;7a) displayed high affinity (IC50 = 2.7 +/- 0.69 microM) and efficacy at muscarinic receptors coupled to PI metabolism in the rat cortex and hippocampus [11].
  • Antibody specificity to the TFA hapten was confirmed in each positive result by a 'hapten inhibition' experiment in which TFA albumin binding was blocked by preincubation of serum with TFA-lysine [12].
  • Most probably this assay detects a relatively low affinity cross-reaction with the TFA hapten of antibodies in the patients' sera which are directed against specific TFA-labelled liver proteins [12].
  • [figure: see text] Under hydrogen pressure, a catalytic amount of palladium(II) trifluoroacetate and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) promoted asymmetric hydrogenation of alpha-fluorinated iminoesters to afford highly enantioenriched beta-fluorinated alpha-amino esters [13].
  • Effect of beta-cyclodextrin on the hydrolysis of trifluoroacetate esters [14].
 

Anatomical context of TRIFLUOROACETATE

 

Associations of TRIFLUOROACETATE with other chemical compounds

  • Separation of proteins, DNA and RNA was carried out by isopycnic centrifugation in cesium trifluoroacetate [20].
  • Xyloglucans synthesised by cultured rose (Rosa sp.) cells in "heavy" or "light" media (with [13C,2H]glucose or [12C,1H]glucose, respectively) had buoyant densities of 1.643 and 1.585 g ml-1, respectively, estimated by isopycnic centrifugation in caesium trifluoroacetate [21].
  • Nanoparticles formulated with lysine polymers having different counterions at the time of DNA mixing have distinct geometric shapes: trifluoroacetate or acetate counterions produce ellipsoids or rods, respectively [22].
  • Sera from 40 patients with a clinical diagnosis of halothane-associated hepatitis were tested for the presence of antibodies to the trifluoroacetate (TFA) halothane metabolite hapten using an ELISA assay, with TFA-albumin as the antigen [12].
  • PBR-MEL (9) (i.e., 670 amu) was synthesized by coupling of two key intermediates: 4-[bis(2-chloroethyl)-amino]-L-phenylalanine ethyl ester trifluoroacetate (6) and 1-(3'-carboxylpropyl)-7-chloro-1,3- dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one (8) [23].
 

Gene context of TRIFLUOROACETATE

  • Preparations of C10 acetate, trifluoroacetate, and chloro derivatives of dicyanocobyrinic acid heptamethyl ester ('cobester') are described [24].
  • [reaction: see text] The concecutive Criegee rearrangement reactions were studied for tert-butyl trifluoroacetate, triarylcarbinols, and benzophenone ketales with trifluoroperacetic acid (TFPAA) in trifluoroacetic acid (TFA) [25].
  • The calculated interchange rate constant k(1)' (Eigen-Wilkins mechanism) increases from the hard O- and N-donors to the soft S-donors, as exemplified by the following series: TFA (trifluoroacetate) (k(1)' = 2.9 x 10(-3) s(-1)) < Br(-) < CH(3)CN < Pyz < THT < DMS < TU (thiourea) (k(1)' = 41.5 x 10(-3) s(-1)) [26].
  • Deaminoarginine-vasopressin (DAVP) and arginine-vasopressin (AVP) have been analyzed as their acetate and trifluoroacetate salts [27].
  • Two types of complexes have been synthesized, i.e., the mono(chelate) complex (1) of the general formula [Ni(o-MeO-dppe)X2] (where X = Cl, Br or I) and the bis(chelate) complex (2) of the general formula [Ni(o-MeO-dppe)2]Y2 (where Y = PF6 or trifluoroacetate (TFA)) [28].
 

Analytical, diagnostic and therapeutic context of TRIFLUOROACETATE

References

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  13. Pd-catalyzed asymmetric hydrogenation of alpha-fluorinated iminoesters in fluorinated alcohol: a new and catalytic enantioselective synthesis of fluoro alpha-amino acid derivatives. Abe, H., Amii, H., Uneyama, K. Org. Lett. (2001) [Pubmed]
  14. Effect of beta-cyclodextrin on the hydrolysis of trifluoroacetate esters. Fernández, M.A., de Rossi, R.H., Cervelló, E., Jaime, C. J. Org. Chem. (2001) [Pubmed]
  15. Xyloglucan undergoes interpolymeric transglycosylation during binding to the plant cell wall in vivo: evidence from 13C/3H dual labelling and isopycnic centrifugation in caesium trifluoroacetate. Thompson, J.E., Smith, R.C., Fry, S.C. Biochem. J. (1997) [Pubmed]
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  19. Hypotensive mechanism of [Leu13]motilin in dogs in vivo and in vitro. Iwai, T., Nakamura, H., Takanashi, H., Yogo, K., Ozaki, K., Ishizuka, N., Asano, T. Can. J. Physiol. Pharmacol. (1998) [Pubmed]
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  24. Chemical behavior of dicyanocob(III)yrinic acid heptamethyl ester and cob(I)yrinic acid heptamethyl ester in some preparative experiments. Inhoffen, H.H., Gossauer, A., Heise, K.P., Laas, H. Philos. Trans. R. Soc. Lond., B, Biol. Sci. (1976) [Pubmed]
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  26. Mechanistic changeover for the water substitution on fac-[(CO)3Re(H2O)3]+ revealed by high-pressure NMR. Grundler, P.V., Salignac, B., Cayemittes, S., Alberto, R., Merbach, A.E. Inorganic chemistry. (2004) [Pubmed]
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