PMID: 6108295May 1, 1980Paper

Solid-phase peptide synthesis of somatostatin using mild base cleavage of N alpha-9-fluorenylmethyloxycarbonylamino acids

International Journal of Peptide and Protein Research
C D ChangJ Meienhofer

Abstract

Experimental details for the "Fmoc solid phase peptide synthesis" of somatostatin are described. The 9-fluorenylmethyloxycarbonyl group was rapidly and quantitatively cleaved by 55% piperidine in dimethylformamide and monitored (u.v.) manually. For a kinetic study, a centrifugal reactor with a photometric control system and reference cell was used at each stage. The symmetrical anhydride coupling reaction was rapid and either acetic anhydride or fluorescamine termination was incorporated to minimize formation of deletion peptides. Anchor-bond cleavage was effected with trifluoroacetic acid which simultaneously removed all the acid labile tert.-butyl side chain protecting groups. N alpha-9-fluorenylmethyloxycarbonyl peptides may be obtained by omitting the piperidine deprotection step after the last cycle of synthesis. From several syntheses, analytically pure di-S-protected somatostatin 14-peptide was obtained in 55-60% overall yield. The S-protecting groups were removed and the product was purified by gel filtration to give homogeneous dihydrosomatostatin (91%) yield. Oxidation of dihydrosomatostatin with potassium ferricyanide and purification by countercurrent distribution provided analytically pure homogeneous somatostatin.

References

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Citations

Mar 1, 1992·International Journal of Peptide and Protein Research·K M SivanandaiahC Renukeshwar
Mar 1, 1990·International Journal of Peptide and Protein Research·G B Fields, R L Noble
Aug 1, 1987·International Journal of Peptide and Protein Research·R RocchiB Scolaro
Jul 29, 1998·Journal of Peptide Science : an Official Publication of the European Peptide Society·F SebestyénA Furka
Dec 1, 1987·International Journal of Peptide and Protein Research·G BaranyD G Mullen
Sep 1, 1990·International Journal of Peptide and Protein Research·D S KingG B Fields
Jul 1, 1990·International Journal of Peptide and Protein Research·F FiliraR Rocchi
Aug 17, 1999·The Journal of Peptide Research : Official Journal of the American Peptide Society·Y D HuangC I Niu
Mar 25, 2005·The Journal of Peptide Research : Official Journal of the American Peptide Society·D B HeadJ A Burton
Aug 1, 1990·International Journal of Peptide and Protein Research·J ShaoW Voelter
Jul 1, 1983·International Journal of Peptide and Protein Research·M TessierJ Van Rietschoten
Feb 1, 1997·The Journal of Peptide Research : Official Journal of the American Peptide Society·R HoffmannH R Kalbitzer
Oct 6, 1997·The Journal of Peptide Research : Official Journal of the American Peptide Society·A BagnoC Di Bello
Sep 8, 2001·Journal of Peptide Science : an Official Publication of the European Peptide Society·J SlaninováZ Procházka
Dec 20, 2005·Journal of Peptide Science : an Official Publication of the European Peptide Society·Toshihiko SakuraiIsao Taniguchi
Aug 1, 1985·European Journal of Biochemistry·R ZaunerS Werner
Feb 24, 2001·Journal of Peptide Science : an Official Publication of the European Peptide Society·R C Jones, J Dickson
Dec 1, 1983·Biopolymers·P PallaiW Vale

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