One-Pot High-Throughput Synthesis of β-Turn Cyclic Peptidomimetics via “Volatilizable” Supports
The Journal of Organic Chemistry2009Vol. 74(5), pp. 2183–2185
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Abstract
A promising method for the high-throughput synthesis of linear C-hydroxyalkylamido peptidomimetics and beta-turn cyclic peptidomimetics via "volatilizable" aminoalkyl functionalized silica gels is presented. Boc amino acids and carboxylic acids were coupled on functionalized aminoalkyl silica gels using a standard DIC/HOBt coupling protocol. After peptide synthesis, the resin bound peptide was cleaved using a two-step process to obtain the linear C-hydroxyalkylamido peptidomimetics. Beta-turn cyclic peptidomimetics were generated by intramolecular S(N)Ar cyclization in an aqueous solution. Both the linear and the cyclic peptidomimetics were obtained with good to excellent yields and purities through a "one-pot" reaction.
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