REFERENCES
- Abbreviations used: Boc = t-butoxycarbonyl, Fmoc = (9-fluorenylmethoxy)carbonyl, Orn = omithine, Z = benzyloxycarbonyl
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- While the reaction of benzyl chlorocarbonate with N-hydroxysuccinimide (HOSu) in equimolar quantities was complete after half an hour, that of 9-fluorenylmethyl chlorocarbonate (Fmoc-Cl) with HOSu requires 20% excess of HOSu and one hour and half to be completed. If there remains unreacted Fmoc-Cl, it reacts with the main product Fmoc-Orn(Boc) (4) to give a reactive mixed anhydride, which in turn reacts with still unreacted Orn(Boc) to furnish dipeptide Fmoc-Orn(Boc)-Orn(Boc). This, after the Boc removal process, yields dipeptide Fmoc-Om-Orn that cannot be removed from the final derivative, Fmoc-Orn (7) which remains as 2% contaminant
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