Fluorenylmethyloxycarbonyl protecting group
The fluorenylmethoxycarbonyl protecting group is a base-labile protecting group used in organic synthesis.Reactions
Fmoc carbamate is frequently used as a protecting group for amines, where the Fmoc group can be introduced by reacting the amine with fluorenylmethyloxycarbonyl chloride, e.g.:
The other common method for introducing the Fmoc group is through 9-fluorenylmethylsuccinimidyl carbonate, which may itself be obtained by the reaction of Fmoc-Cl with the dicyclohexylammonium salt of N-hydroxysuccinimide.
It may be cleaved by bases, typically a solution of piperidine:
Fmoc protection has found significant use in solid phase peptide synthesis because its removal with piperidine solution does not disturb the acid labile linker between the peptide and the resin.
Because the fluorenyl group is highly fluorescent, certain UV-inactive compounds may be reacted to give the Fmoc derivatives, suitable for analysis by reversed phase HPLC. Analytical uses of Fmoc-Cl that do not use chromatography may be limited by the requirement that excess Fmoc-Cl be removed before an analysis of fluorescence.Common amine protection methods
