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Solutions For An Introduction to Medicinal Chemistry Chapter 1 Problem 2Q

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Solution 1

Valinomycin is a peptide which is used in the transport of potassium ions and is a potent antibiotic. In the cell membrane, it shows high selectivity for potassium ions over sodium ions. It acts specifically as a potassium transporter, allowing the transport of potassium ions through lipid membranes.

Valinomycin is made of twelve amino acids alternating with each other and esters to form a macromolecule. There are 12 carbonyl groups present, which are essential for solvation in solvent. On the other hand, different isopropyl and methyl groups are also present, which are responsible for solvation in non-polar solvents.

Valinomycin is a carrier for potassium. This antibiotic is highly selective for potassium ion relative to sodium ion. The sodium ion, which is smaller in size, interacts with all the six oxygen atoms present in the valinomycin.

Henceforth, it is not suitable for sodium ion to form complex with valinomycin due to its low hydration energy. Puckering of the ring and its stability due to the presence of hydrogen bonds allows it to closely surround a single anhydrate potassium ion.

Figure: Valinomycin

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