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Issue 23, 1998
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Preparation and metal ion-binding properties of gramicidin S derivatives carrying picolinoyl groups on the ornithine side chains

Abstract

Derivatives of gramicidin S (GS) in which one or both of the two ornithine side chains were picolinoylated were prepared. The dipicolinoyl derivative [Orn(PyCO)2,2′]GS 1 formed a 1∶1 complex with Cu2+ and Zn2+ in MeOH, while in the case of the monopicolinoyl derivative [Orn(Boc)2,Orn(PyCO)2′]GS (2) stepwise formation of 1∶1 and 2∶1 (2∶Cu2+) complexes was observed. The formation constant of the Cu2+-mediated dimeric species of compound 2 was larger than those of the corresponding linear compounds possessing the partial structure of macrocycle 2. The corresponding tetra-N-methyl derivative [MeOrn(Boc)2,MeOrn(PyCO)2′,D-MePhe4,4′]GS 3 also showed lower stability of the 2∶1 complex compared with compound 2, which suggested the presence of a β-sheet-type intermolecular H-bonding interaction between the two molecules of macrocycle 2 in the 2∶1 complex.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1998, 3999-4004
Article type
Paper

Preparation and metal ion-binding properties of gramicidin S derivatives carrying picolinoyl groups on the ornithine side chains

K. Yamada, H. Ozaki, N. Kanda, H. Yamamura, S. Araki and M. Kawai, J. Chem. Soc., Perkin Trans. 1, 1998, 3999
DOI: 10.1039/A805468A

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