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p-Chlorotetrafluorophenyl esters of N-protected amino acids
V N Medvedkin1, L N Klimenko, Y V Mitin
1Institute of Protein Research, Russian Academy of Science, Pushchino, Moscow Region.
Abstract:
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.