McGimpsey, W. Grant.
A network of amide and ester linkages were used to create an ammonium ionophore using solution state chemistry. One target ionophore (1) was created in its entirety, and the building blocks (Blocks I, II, III and IV) for two other ionophores (2,3) were synthesized but were not assembled fully into ionophores. Fmoc, t-Boc and benzyl protection strategies were used to protect the amide and ester network. The binding site of compound 1 was synthesized from L-lactic acid, benzyl alcohol, Boc-D-Val-OH, D-hydroisovaleric acid, and L-lysine (Fmoc). These compounds were combined to first create a linear compound which was then cyclized to form the ionophore. Compound 1 was synthesized by coupling the cyclic ionophore to 11-mercaptoundecanoic acid, thereby allowing its deposition on a gold surface. Yields 0.38g. The partial synthesis of compound 2 that was completed involved the coupling of L-Lactic Acid, Benzyl alcohol, Boc-D-Val-OH, D-hydroisovaleric acid and L-Dap (Fmoc) to form the linear precursor. Yields 5.31g. Partial synthesis of compound 3 was achieved, using the same methods as compound 1.
Worcester Polytechnic Institute
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Chemistry and Biochemistry