Optimized preparation of deca(L-Alanyl)-L-valinamide by 9-fluorenylmethyloxycarbonyl (fmoc) solid-phase synthesis on polyethylene glycol-polystyrene (PEG-PS) graft supports, with 1,8-diazobicyclo[5.4.0]-undec-7-ene (DBU) deprotection

Steven A. Kates, Nuria A. Solé, Michael Beyermann, George Barany, Fernando Albericio

Research output: Contribution to journalArticlepeer-review

68 Scopus citations

Abstract

Deca(L-alanyl)-L-valinamide is known to be a challenging model target for solidphase peptide synthesis, due to its hydrophobicity and its tendency to form secondary structures which inhibit acytation and deprotection. Here we report systematic studies on the synthesis of this peptide on an automated continuous-flow instrument, using the 9-fluorenylmethyloxycarbonyl (Fmoc) group for Nα-amino protection and a polyethylene-glycol polystyrene (PEG-PS) graft support. The optimal deprotection reagent proved to be DBU-piperidine-DMF (1:1:48, vol/vol/vol). The synthetic peptides were analyzed and characterized by high-performance liquid chromatography and several mass spectrometric techniques.

Original languageEnglish (US)
Pages (from-to)106-113
Number of pages8
JournalPeptide research
Volume9
Issue number3
StatePublished - 1996

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