Cyclic tetrapeptides have potential applications in pharmaceutical research and development. While naturally occurring cyclic peptides are noted for their medical usefulness, they are also recognized for their synthetic challenge. The reactions studied involve the synthesis of a symmetric cyclic 12-membered bis-lactam; the route developed here will be utilized to later synthesize cyclic tetrapeptides. The synthesis presented consists of 5 steps. First, 5-aminovaleric acid is coupled to salicaldehyde by reductive amination using sodium borohydride. This step is followed by protection of the free amine as the benzyloxy carbamate (Z). The key step of this synthetic approach involves the formation of a dimer of N-Z-N-(2-hydroxybenzyl)-5-amino-valeric acid . The conditions of this dimerization will be discussed in further detail on the poster. After removal of the benzyloxy carbonyl protecting group and double ring contraction, we will obtain a bis-lactam as our model compound. Modification of the initial amino acid starting material will allow us to synthesize a variety of symmetric cyclic tetrapeptides.
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