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

Authors
KATES SA SOLE NA BEYERMANN M BARANY G ALBERICIO F
Citation
Sa. Kates et al., 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, Peptide research, 9(3), 1996, pp. 106-113
Citations number
50
Categorie Soggetti
Biology
Journal title
Peptide research → ACNP
ISSN journal
10405704
Volume
9
Issue
3
Year of publication
1996
Pages
106 - 113
Database
ISI
SICI code
1040-5704(1996)9:3<106:OPODB9>2.0.ZU;2-9
Abstract
Deca(L-alanyl)-L-valinamide is known to be a challenging model target for solid-phase peptide synthesis, due to its hydrophobicity and its t endency reform secondary structures which inhibit acylation and deprot ection. Here we report systematic studies on the synthesis of this pep tide on an automated continuous-flow instrument, using the 9-fluorenyl methyloxycarbonyl (Fmoc) group for N-alpha-amino protection and a poly ethylene-glycol polystyrene (PEG-PS) graft support. The optimal deprot ection reagent proved to be DBU-piperidine-DMF (1:1:48, vol/vol/vol). The synthetic peptides were analyzed and characterized by high-perform ance liquid chromatography and several mass spectrometric techniques.