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Org Lett. 2012 Jun 1;14(11):2774-7. doi: 10.1021/ol3010003. Epub 2012 May 11.

Microwave assisted synthesis of Py-Im polyamides.

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1
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.

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 α-amino acid does not racemize after several additional coupling steps.

PMID:
22578091
PMCID:
PMC3365540
DOI:
10.1021/ol3010003
[Indexed for MEDLINE]
Free PMC Article
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