Synthesis of lysine-valinomycin by solid-phase segment condensation.
In order to obtain a readily derivatized analog of the ionophore antibiotic valinomycin, [1-lysine] valinomycin (Lys-VAL) was synthesized. The compound was built up on a polystyrene support by stepwise segment condensation and was cyclized in solution. The segments used were didepsipeptides protected by the t-butyloxycarbonyl and p-nitrobenzyloxycarbonyl groups. Derivatives prepared by acylation of the epsilon-amino group of Lys-VAL included [14C]acetyl-Lys-VAL, dansyl-Lys-VAL, palmitoyl-Lys-VAL and dithiodiglycoyl-bis-Lys-VAL. These derivatives had a high potassium binding capacity but were in general much less active than VAL in mediating ion transport in membranes.
D000595:Amino Acid Sequence; D055598:Chemical Phenomena; D002621:Chemistry; D003500:Cyclization; D007476:Ionophores; D008239:Lysine / Q000138:chemical synthesis*; D008563:Membrane Lipids / Q000378:metabolism; D008722:Methods; D011188:Potassium / Q000378:metabolism; D014634:Valinomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism
D007476:Ionophores; D008563:Membrane Lipids; D014634:Valinomycin; D008239:Lysine; D011188:Potassium