Vn. Medvedkin et al., P-CHLOROTETRAFLUOROPHENYL ESTERS OF N-PROTECTED AMINO-ACIDS, International journal of peptide & protein research, 44(5), 1994, pp. 477-484
p-Chlorotetrafluorophenyl (Tfc) esters of protected amino acids and pe
ptides are more reactive than are the well known pentafluorophenyl (Pf
p) esters, Two reagents, p-chlorotetrafluorophenyltrifluoroacetate (Tf
c-OTfa) and di-(p-chlorotetrafluorophenyl)carbonate (di-Tfc-carbonate)
, can be used for their syntheses, thereby avoiding use of the allergi
c dicyclohexylcarbodiimide. This is especially important for bulk prep
arations. Many Fmoc- and Boc-amino acid-OTfc esters have been synthesi
zed and characterized. The hexadecameric tandem repeat H-(AlaAlaLysPro
)(4)-OH was synthesized using di-Tfc-carbonate for the preparation of
Tfc-esters. (C) Munksgaard 1994.