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Microwave assisted synthesis of Py-Im polyamides.

ABSTRACT: Microwave synthesis was utilized to rapidly build Py-Im polyamides in high yields and purity using Boc-protection chemistry on Kaiser oxime resin. A representative polyamide targeting the 5'-WGWWCW-3' (W = A or T) subset of the consensus Androgen and Glucocorticoid Response Elements was synthesized in 56% yield after 20 linear steps and HPLC purification. It was confirmed by Mosher amide derivatization of the polyamide that a chiral ?-amino acid does not racemize after several additional coupling steps.

SUBMITTER: Puckett JW

PROVIDER: S-EPMC3365540 | biostudies-literature | 2012 Jun

REPOSITORIES: biostudies-literature

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Microwave assisted synthesis of Py-Im polyamides.

Puckett James W JW Green Joshua T JT Dervan Peter B PB

Organic letters 20120511 11

Microwave synthesis was utilized to rapidly build Py-Im polyamides in high yields and purity using Boc-protection chemistry on Kaiser oxime resin. A representative polyamide targeting the 5'-WGWWCW-3' (W = A or T) subset of the consensus Androgen and Glucocorticoid Response Elements was synthesized in 56% yield after 20 linear steps and HPLC purification. It was confirmed by Mosher amide derivatization of the polyamide that a chiral α-amino acid does not racemize after several additional couplin ...[more]

PMID: 22578091

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