Valinomycin analogues

Kuisle, O., Quinoa, E., and Riguera, R., (1999) A general methodology for automated solid-phase synthesis of depsides and depsipeptides. Preparation of a valinomycin analogue. J. Org Chem. 64, 8063-8075. 

An extensive range of synthetic analogues of valinomycin and the enniatins has been prepared and investigated these studies have been fully described in ai monograph.532 Synthetic peptides have also been prepared and their complexing properties investigated for example [L-Val-D-Pro-D-Val-L-Pro]3 reacts with potassium picrate to give an isolable 1 1 complex which is expected to have a structure similar to that of the K+ complex of (137).557 More detailed studies have been made on the complexation properties of the small synthetic peptides [L-Pro-Gly]3 and [L-Pro-Gly]4. 

A range of cyclic peptide analogues of valinomycin have been synthesized having proline and valine residues. For PV [cyc/o (-Val-Pro-Val-Pro-)3J, PV-10 [cyc/o(-Pro-Val-Pro-Val-)2-Pro-Val] and PV-8 [cyc/o(-Pro-Val-Pro-Val-)2] the preference for K+ over Na+ was 700, 5 and <1 respectively, showing how selectivity depends upon the ring size.36... 

Similar studies were carried out on other enniatin analogues [617], enniatin itself [618] and valinomycin [619]. The Ca complexes of a series of C3 symmetric trispeptides were also modeled, and it was shown that some of these have the ability to form chiral Ca complexes [621]. 

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