N-9-fluorenylmethoxycarbonylpyroglutamate. Preparation of the acid, chloride and succinimidyl ester.
Fmoc-glutamic acid is converted by thionyl chloride into the dichloride, which spontaneously cyclizes to Fmoc-pyroglutamyl chloride. The latter is stable to water. Pure Fmoc-pyroglutamyl chloride is obtained by washing the reaction mixture with water, which destroys uncyclized dichloride by converting it into the 2-alkoxy-5(4H)-oxazolone that is readily hydrolyzed. Fmoc-pyroglutamic acid and succinimidyl ester are obtained from the chloride by acid hydrolysis and reaction with N-hydroxysuccinimide, respectively.
Benoiton
N L
NL
Department of Biochemistry, University of Ottawa, Ontario, Canada.
Chen
F M
FM
D005449:Fluorenes / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011761:Pyrrolidonecarboxylic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D013388:Succinimides / Q000737:chemistry*; D013461:Sulfur Oxides / Q000737:chemistry*
D005449:Fluorenes; D013388:Succinimides; D013461:Sulfur Oxides; C054798:9-fluoroenylmethoxycarbonylpyroglutamate; C023589:thionyl chloride; C001426:N-hydroxysuccinimide; D011761:Pyrrolidonecarboxylic Acid