PMID: 2198236May 1, 1990Paper

Repetitive BOP coupling (REBOP) in solid phase peptide synthesis. Luliberin synthesis as model

International Journal of Peptide and Protein Research
R SeyerB Castro


The coupling reagent (benzotriazol-1-yloxy)tris-(dimethylamino)phosphonium (BOP) hexafluorophosphate was tested in the synthesis of luliberin (LH-RH) with inexpensive classically protected Boc-amino acids, in slight excess, and benzhydryl amino resin, without any other additive. The good solubility of this reagent and its by-products is of particular interest for automated peptide synthesis. [D-His2]LH-RH was also synthesized and compared with LH-RH by proton nuclear magnetic resonance spectroscopy. As shown by the biological tests and the high performance liquid chromatography study, unprotected pyroGlu and Boc-His can be used without any significant racemization but Boc-His(Boc) was found to be preferable since it gave no detectable racemization and no by-products. The difficult isolation of the minority D-derivative from the crude preparation of LH-RH was resolved by a recycling procedure in reversed phase HPLC.


Sep 1, 1976·Journal of Reproduction and Fertility·M C Viguier-Martinez
Nov 15, 1975·Experientia·P Cordopatis, D Theodoropoulos
Sep 1, 1989·International Journal of Peptide and Protein Research·R SeyerB Castro
Jul 15, 1986·European Journal of Biochemistry·K V CharyG Govil
Jul 1, 1987·Journal of Hypertension. Supplement : Official Journal of the International Society of Hypertension·P EggenaA M Morin
Apr 1, 1973·Analytical Biochemistry·A M Felix, M H Jimenez
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Sep 1, 1970·The Journal of Organic Chemistry·J ScotchlerA B Robinson
Dec 1, 1966·Analytical Chemistry·R B MerrifieldN Jernberg
Jan 1, 1980·Reproduction, Nutrition, Development·A CaratyM P Dubois
Nov 1, 1981·International Journal of Peptide and Protein Research·S S WangR B Merrifield
Mar 1, 1980·International Journal of Peptide and Protein Research·J H JonesM J Witty

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Oct 3, 1999·Journal of Peptide Science : an Official Publication of the European Peptide Society·K YoshidaH Aoyagi

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