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Indium-mediated diastereoselective allylation of D- and L-glyceraldimines with 4-bromo-1,1,1-trifluoro-2-butene: highly stereoselective synthesis of 4,4,4-trifluoroisoleucines and 4,4,4-trifluorovaline.
Chen Q, Qiu XL, Qing FL. Chen Q, et al. J Org Chem. 2006 May 12;71(10):3762-7. doi: 10.1021/jo0601157. J Org Chem. 2006. PMID: 16674047
A practical and efficient route for the stereoselective synthesis of (2R,3S)- and (2S,3R)-4,4,4-trifluoroisoleucines and (2R,3S)-4,4,4-trifluorovaline was developed. Indium-mediated allylation of (R)-N-benzyl-2,3-O-isopropylideneglyceraldimine 7 with 4 …
A practical and efficient route for the stereoselective synthesis of (2R,3S)- and (2S,3R)-4,4,4-trifluoroisoleucines and (2R,3S)-4, …
Fluorinated beta-sheet breaker peptides.
Loureiro JA , Crespo R , Börner H , Martins PM , Rocha FA , Coelho M , Pereira MC , Rocha S . Loureiro JA , et al. J Mater Chem B. 2014 Apr 28;2(16):2259-2264. doi: 10.1039/c3tb21483d. Epub 2014 Mar 14. J Mater Chem B. 2014. PMID: 32261713
The peptides were based on the sequence LVFFD, in which valine was substituted by either 4,4,4-trifluorovaline or 4-fluoroproline, or the phenylalanine at position 3 was replaced by 3,4,5-trifluorophenylalanine. ...
The peptides were based on the sequence LVFFD, in which valine was substituted by either 4,4,4-trifluorovaline o …
Oxazoline-oxazinone oxidative rearrangement. divergent syntheses of (2S,3S)-4,4,4-trifluorovaline and (2S,4S)-5,5,5-Trifluoroleucine.
Pigza JA, Quach T, Molinski TF. Pigza JA, et al. J Org Chem. 2009 Aug 7;74(15):5510-5. doi: 10.1021/jo900654y. J Org Chem. 2009. PMID: 19537688
Stereoselective syntheses of the valuable fluorinated amino acids (2S,3S)-4,4,4-trifluorovaline and (2S,4S)-5,5,5-trifluoroleucine have been achieved starting from 4,4,4-trifluoro-3-methylbutanoic acid by using a conceptually simple transformation: con …
Stereoselective syntheses of the valuable fluorinated amino acids (2S,3S)-4,4,4-trifluorovaline and (2S,4S)-5,5, …
A coiled coil with a fluorous core.
Bilgiçer B, Fichera A, Kumar K. Bilgiçer B, et al. J Am Chem Soc. 2001 May 16;123(19):4393-9. doi: 10.1021/ja002961j. J Am Chem Soc. 2001. PMID: 11457223
All four leucine residues (a position) and three valine residues (d position) were replaced by the unnatural amino acids 5,5,5-trifluoroleucine and 4,4,4-trifluorovaline, respectively. The peptide is highly alpha-helical at low micromolar concentration …
All four leucine residues (a position) and three valine residues (d position) were replaced by the unnatural amino acids 5,5,5-trifluoroleuc …
phi-Values beyond the ribosomally encoded amino acids: kinetic and thermodynamic consequences of incorporating trifluoromethyl amino acids in a globular protein.
Horng JC, Raleigh DP. Horng JC, et al. J Am Chem Soc. 2003 Aug 6;125(31):9286-7. doi: 10.1021/ja0353199. J Am Chem Soc. 2003. PMID: 12889945
The consequences of the substitution of 4,4,4-trifluorovaline for valine on the folding kinetics and thermodynamics of a globular protein are presented. ...
The consequences of the substitution of 4,4,4-trifluorovaline for valine on the folding kinetics and thermodynam …
Stabilization of bzip peptides through incorporation of fluorinated aliphatic residues.
Son S, Tanrikulu IC, Tirrell DA. Son S, et al. Chembiochem. 2006 Aug;7(8):1251-7. doi: 10.1002/cbic.200500420. Chembiochem. 2006. PMID: 16758500
Two fluorinated amino acids, 5,5,5-trifluoroisoleucine (5TFI) and (2S,3R)-4,4,4-trifluorovaline (4TFV), which have been shown to serve as isoleucine surrogates in protein synthesis in Escherichia coli, have been incorporated in vivo into basic leucine …
Two fluorinated amino acids, 5,5,5-trifluoroisoleucine (5TFI) and (2S,3R)-4,4,4-trifluorovaline (4TFV), which ha …