Synthesis and characterization of Tyr(Bzl)9,11,13,15 and Tyr9,11,13,15 gramicidin A.

Tyr(Bzl) and Tyr gramicidin A were prepared by the solid phase method using a 4-(oxymethyl)-Pam resin and Bpoc as alpha-amino-protecting group. The benzylated analog [Gr.T(Bzl)] was purified by chromatography on silica gel and then on LH60 Sephadex. Removal of benzyl groups was carried out by hydrogenolysis and the debenzylated derivative (Gr.T) was purified in the same way. Both gramicidins were checked and characterized by t.l.c., HPLC, circular dichroism, 1H n.m.r. and single channel measurements. CD spectra were found to be different for Gr.T(Bzl) and Gr.T and strongly dependent upon the solvent and the concentration. Single channel conductance of Gr. T is slightly lower than that of Gr.A (A Gr.T approximately equal to 0.7 A Gr.T).