Collect. Czech. Chem. Commun. 1992, 57, 1707-1718

Solid Phase Synthesis of a Somatostatin Amide Analogue Using Acid Labile t-Bumeoc Protection and an Acid Labile Anchor Group

Wolfgang Voeltera, Gerhard Breipohlb, Chryssa Tzougrakic and Eveline Jungfleisch-Turguta

a Abteilung für Physikalishe Biochemie des Physiologisch-chemischen Instituts der Universität Tübingen, Hoppe-Seyler Str. 4, D-7400 Tübingen, Germany
b Hoechst AG, P.O. Box 80 03 20, W-6230 Frankfurt 80, Germany
c University of Athens, Department of Chemistry, Panepistimiopolis, Zographou, GR-157710680 Athens, Greece


The solid phase synthesis of an amidated somatostatin analogue based on the principle of differentiated acidolysis is described. The acid labile and smoothly cleavable t-Bumeoc moiety (1% TFA/DCM) is used for temporary Nα-protection of D- and L-amino acids and [4-[[[9H-fluoren-9-yl-methoxycarbonyl]amino](4-methoxyphenyl)methyl]-2-methylphenoxy]acetic acid, attached to an aminomethylated polystyrene resin is used as acid sensitive linker of the solid carrier which releases the peptide in its amide form by treatment with TFA. Its preparation is described in detail.