Synthesis of analogs of valinomycin and enniatine B containing charged, spin-labeled, or fluorescent groups

Sandwich complexes as a functional form of the enniatin ionophores

“…8). 'bis-Enniatin B' was synthesized in a 26% yield by the acid chloride method starting from enniatin B analogues with an N-methyl-L-glutamic acid or N-methyl-L-lysine residue instead of one of the N-methyl L-valine residues [7]; [a]$23.3 (c 0.1% in EtOH).…”

Second febs—ferdinand springer lecture membrane active complexones. chemistry and biological function

“…However, structural peculiarities of the valinomycin analogs (XXVII and XL, see below) caused them considerable sluggishness at one or another of the transmembrane transporting stages which were thereby brought to light and thus included in our model. We aim to continue our studies on the behavior of valinomycin on artificial membranes, making use of the recently synthesized spin-and fluorescence- labeled derivatives II and III [4] , which turned out practically identical to valinomycin in their ability to transport potassium ions across lecithin micelles (table 1).…”

Isotopic Mass-Dependent MS-Patch-Clamp and Isotopic Mass-Independent ESR-Patch-Clamp

“…For example, from the beginning of the ESR-technique development, biophysicists have accepted the spin labeling technique for the simplest ion channels, such as spin-labeled derivatives of gramicidin peptides [162] and spin-labeled gramicidin itself [163], labeled valinomycin and its analogs [164] (along with the NMR observations of the nuclear Overhauser effect of transfer of the nuclear spin polarization from one nuclear spin population to another one via cross-relaxation [165,166]; the same method has been applied to the gramicidin [167][168][169]), cecropin [170][171][172][173], zervamicin [174,175] (early labeled by deuterium [176], 13 C and 15 N for NMR measurements [177]), alamethicin [178][179][180][181][182], etc. It is noteworthy that gramicidin as well as valinomycin [183] are well known as the simple ion channels [184][185][186][187][188], which can be studied by spin labeling and magnetic resonance methods [189,190] (as well as ion-channel-forming valinomycin [191][192][193]); zervamicin is also well known as the ion-channel-forming agent, ion channel peptide and a good model for the membrane ion channels [194][195][196] with a well-studied gating mechanisms [197][198][199] which can operate not only in the native membranes, but also in the artificial micelles and lipid bilayers…”