论文信息 - p-Chlorotetrafluorophenyl esters of N-protected amino acids.

p-Chlorotetrafluorophenyl esters of N-protected amino acids.

p-Chlorotetrafluorophenyl (Tfc) esters of protected amino acids and peptides are more reactive than are the well known pentafluorophenyl (Pfp) esters. Two reagents, p-chlorotetrafluorophenyltrifluoroacetate (Tfc-OTfa) and di-(p-chlorotetrafluorophenyl)carbonate (di-Tfc-carbonate), can be used for their syntheses, thereby avoiding use of the allergic dicyclohexylcarbodiimide. This is especially important for bulk preparations. Many Fmoc- and Boc-amino acid-OTfc esters have been synthesized and characterized. The hexadecameric tandem repeat H-(AlaAlaLysPro)4-OH was synthesized using di-Tfc-carbonate for the preparation of Tfc-esters.

[1] S. Permyakov,et al. Kinetics of peptide synthesis studied by fluorescence of fluorophenyl esters. , 2009, International journal of peptide and protein research.

[2] J. Yates,et al. Tandem quadrupole Fourier-transform mass spectrometry of oligopeptides and small proteins. , 1987, Proceedings of the National Academy of Sciences of the United States of America.

[3] M. Bodanszky,et al. Active Esters and the Strategy of Peptide Synthesis , 1973 .

[4] R. H. Johnson,et al. Synthesis of N-carbobenzoxyamino acid and peptide pentafluorophenyl esters as intermediates in peptide synthesis. , 1970, The Journal of organic chemistry.

[5] T. Wieland,et al. Über Peptidsynthesen, XXIV. Derivate der Kohlensäure in der Peptidchemie , 1962 .

[6] M. Bodanszky. Synthesis of Peptides by Aminolysis of Nitrophenyl Esters , 1955, Nature.