Improved routes to tetrabenzo[a,c,g,i]fluorene derivatives have been
developed, allowing the synthesis of Nᵃ-17-tetrabenzo[a,c,g,i]fluorenylmethoxycarbonyl (Tbfmoc) urethane derivatives of alanine, leucine, isoleucine,
methionine and valine. The chloroformate and pentafluorophenyl carbonate of 17-
tetrabenzo[a,c,g,i]fluorenylmethanol have been prepared and used to introduce the
base-labile Tbfmoc group onto the Nᵃ-termini of resin-bound peptides.The high affinity of the Tbfmoc group for porous graphitised carbon (PGC)
has been exploited for the purification of a range of synthetic peptides (23-85
residues). A comparison of various basic solvent sytems used to elute the purified
peptide from PGC is presented. The hydrophobicity of the Tbfmoc group has been
used to simplify the purification of a ubiquitin analogue, UbY59F (76 residues), by
the enhanced retention of the Tbfmoc peptide on RP-HPLC.A new synthesis of 2-hydroxydibenzocycloheptadien-5-one has been devised.
This compound has been used to develop acid-labile linkers for the synthesis of
peptide C-terminal alkyl amides and aza-glycine peptides, compatible with the
FmocABu solid phase method. Alternative modes of attachment of the linker to
polystyrene resin are compared for the synthesis of bombesin, a peptide amide
