Syntheses and antibacterial activities of gramicidin S analogs containing L-ornithine in place of L-valine.
A gramicidin S analog ([Orn1,1']GS.4HCl) containing L-ornithine in place of L-valine at the 1,1' positions was synthesized by the conventional solution method in order to examine whether this analog had antibacterial activity toward Gram-negative bacteria. In the synthesis of [Orn1,1']GS.4HCl, two intermediate analogs ([Orn1,1', Orn(For)2,2']GS.2HCl and [Orn(Z)1,1']GS.2HCl) were obtained. [Orn1,1']GS.4HCl and [Orn1,1', Orn(For)2,2']GS.2HCl showed no activity toward either Gram-negative or Gram-positive bacteria, whereas [Orn(Z)1,1']GS.2HCl showed appreciable activity toward only Gram-positive bacteria.
Soejima
Y
Y
Laboratory of Biochemistry, Faculty of Engineering, Kyushu Sangyo University, Fukuoka, Japan.
Hashiguchi
A
A
Izumiya
N
N
D000595:Amino Acid Sequence; D001412:Bacillus subtilis / Q000187:drug effects; D001709:Biotechnology; D004352:Drug Resistance, Microbial; D004926:Escherichia coli / Q000187:drug effects; D006096:Gramicidin / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D008969:Molecular Sequence Data; D011487:Protein Conformation; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship
D006096:Gramicidin