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One-pot high-throughput synthesis of beta-turn cyclic peptidomimetics via "volatilizable" supports.

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.

SUBMITTER: Li Y

PROVIDER: S-EPMC3117271 | biostudies-literature | 2009 Mar

REPOSITORIES: biostudies-literature

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One-pot high-throughput synthesis of beta-turn cyclic peptidomimetics via "volatilizable" supports.

Li Yangmei Y Yu Yongping Y Giulianotti Marc M Houghten Richard A RA

The Journal of organic chemistry 20090301 5

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 cy ...[more]

PMID: 19173629

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