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Solid phase synthesis of polyamides containing imidazole and pyrrole amino acids

Baird, Eldon E. and Dervan, Peter B. (1996) Solid phase synthesis of polyamides containing imidazole and pyrrole amino acids. Journal of the American Chemical Society, 118 (26). pp. 6141-6146. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20160510-103835386

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Abstract

The solid phase synthesis of sequence specific DNA binding polyamides containing N-methylimidazole (Im) and N-methylpyrrole (Py) amino acids is described. Two monomer building blocks, Boc-Py-OBt ester and Boc-Im acid, are prepared on a 50 g scale without column chromatography. Using commercially available Boc-beta-alanine-Pam resin, cycling protocols were optimized to afford high stepwise coupling yields (>99%). Deprotection by aminolysis affords up to 100 mg quantities of polyamide. Solid phase methodology increases both the number and complexity of minor groove binding polyamides which can be synthesized and analyzed with regard to DNA binding affinity and sequence specificity. The solid phase synthesis of a representative eight-residue polyamide is reported.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja960720zDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja960720zPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja960720zPublisherSupporting Information
Additional Information:© 1996 American Chemical Society. Received March 5, 1996. Publication Date (Web): July 3, 1996. Abstract published in AdVance ACS Abstracts, June 15, 1996. We are grateful to the National Institutes of Health (GM-27681) for grant support and the Howard Hughes Medical Institute for a predoctoral fellowship to E.E.B.
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Funding AgencyGrant Number
NIHGM-27681
Howard Hughes Medical Institute (HHMI)UNSPECIFIED
Record Number:CaltechAUTHORS:20160510-103835386
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20160510-103835386
Official Citation:Solid Phase Synthesis of Polyamides Containing Imidazole and Pyrrole Amino Acids Eldon E. Baird and Peter B. Dervan Journal of the American Chemical Society 1996 118 (26), 6141-6146 DOI: 10.1021/ja960720z
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:66889
Collection:CaltechAUTHORS
Deposited By: Victoria Brennan
Deposited On:18 May 2016 19:19
Last Modified:18 May 2016 19:19

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