Microwave assisted synthesis of Py-Im polyamides.

Organic Letters
James W PuckettPeter B Dervan

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.

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Citations

May 15, 2013·Bioorganic & Medicinal Chemistry·Meghan S Blackledge, Christian Melander
Jan 16, 2013·Proceedings of the National Academy of Sciences of the United States of America·Fei YangPeter B Dervan
Sep 19, 2012·Proceedings of the National Academy of Sciences of the United States of America·Jevgenij A RaskatovPeter B Dervan
Feb 28, 2013·Molecular Cancer Therapeutics·Nicholas G NickolsPeter B Dervan
Nov 17, 2015·PloS One·Amanda E HargrovePeter B Dervan
Apr 9, 2017·Bioorganic & Medicinal Chemistry Letters·Naoki ShigaTetsuhiro Nemoto
Jul 19, 2014·Journal of the American Chemical Society·Akiyoshi HirataHiroshi Sugiyama
Feb 23, 2013·Organic & Biomolecular Chemistry·Waleed M HusseinMariusz Skwarczynski
Nov 3, 2016·Proceedings of the National Academy of Sciences of the United States of America·Liang XuDong Wang
Feb 8, 2014·Journal of the American Chemical Society·JeenJoo S KangPeter B Dervan
Sep 11, 2013·Journal of Medicinal Chemistry·Fei YangPeter B Dervan
Oct 31, 2012·The Journal of Organic Chemistry·Benjamin C LiPeter B Dervan

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Methods Mentioned

BETA
acetylation

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