In order to investigate the contribution of configurations of amino acid residues around Pro residues in gramicidin S to its activity and conformation, [d-Val1,1′]- and [d-Val1,1′ l-Phe4,4′]-gramicidin S were synthesized by a liquid-phase method. The CD spectra of these analogs and gramicidin S in aqueous solutions differ from each other, indicating that these peptides have different conformations. These analogs have practically no activity against the Gram-positive microorganisms tested, indicating the importance of the presence of the d-Phe–Pro–Val sequence in gramicidin S regarding activity.
Die Synthese der Titelverbindungen (Ib) bzw. (Ic), Analoge von Gramicidin S (Ia), erfolgt ausgehend von den (schrittweise nach üblichen Methoden aufgebauten) Bausteinen (IIa) [bzw. den Folgeprodukten (IIb) und (IIc)] bzw. (Va) [bzw. den Folgeprodukten (Vb) und (Vc)] sukzessiv über die jeweils angegebenen Stufen.
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