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Fmoc solid phase synthesis of polyamides containing pyrrole and imidazole amino acids

Wurtz, Nicholas R. and Turner, James M. and Baird, Eldon E. and Dervan, Peter B. (2001) Fmoc solid phase synthesis of polyamides containing pyrrole and imidazole amino acids. Organic Letters, 3 (8). pp. 1201-1203. ISSN 1523-7060. https://resolver.caltech.edu/CaltechAUTHORS:20160510-082731223

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Abstract

Polyamides containing N-methylimidazole (Im) and N-methylpyrrole (Py) amino acids are synthetic ligands that have an affinity and specificity for DNA comparable to those of many naturally occurring DNA binding proteins. A machine-assisted Fmoc solid phase synthesis of polyamides has been optimized to afford high stepwise coupling yields (>99%). Two monomer building blocks, Fmoc-Py acid and Fmoc-Im acid, were prepared in multigram scale. Cleavage by aminolysis followed by HPLC purification affords up to 200 mg quantities of polyamide with purities and yields greater than or equal to those reported using Boc chemistry. A broader set of reaction conditions will increase the number and complexity of minor groove binding polyamides which may be prepared and help ensure compatibility with many commercially available peptide synthesizers.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ol0156796DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ol0156796PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ol0156796PublisherSupporting Information
ORCID:
AuthorORCID
Dervan, Peter B.0000-0001-8852-7306
Additional Information:© 2001 American Chemical Society. Received February 7, 2001; Publication Date (Web): March 28, 2001. We are grateful to the National Institute of Health for research support, the Ralph M. Parsons Foundation for a predoctoral fellowship for N.R.W., J. Edward Richter for an undergraduate fellowship to J.M.T., and the Howard Hughes Medical Institute for a predoctoral fellowship to E.E.B.
Funders:
Funding AgencyGrant Number
NIHUNSPECIFIED
Ralph M. Parsons FoundationUNSPECIFIED
J. Edward RichterUNSPECIFIED
Howard Hughes Medical Institute (HHMI)UNSPECIFIED
Issue or Number:8
Record Number:CaltechAUTHORS:20160510-082731223
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160510-082731223
Official Citation:Fmoc Solid Phase Synthesis of Polyamides Containing Pyrrole and Imidazole Amino Acids Nicholas R. Wurtz, James M. Turner, Eldon E. Baird, and Peter B. Dervan Organic Letters 2001 3 (8), 1201-1203 DOI: 10.1021/ol0156796
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:66826
Collection:CaltechAUTHORS
Deposited By: Victoria Brennan
Deposited On:18 May 2016 19:14
Last Modified:26 Nov 2019 11:15

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