Solid phase synthesis of polyamides containing imidazole and pyrrole amino acids
- Creators
- Baird, Eldon E.
-
Dervan, Peter B.
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.
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.Attached Files
Supplemental Material - ja6141.pdf
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Additional details
- Eprint ID
- 66889
- Resolver ID
- CaltechAUTHORS:20160510-103835386
- GM-27681
- NIH
- Howard Hughes Medical Institute (HHMI)
- Created
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2016-05-18Created from EPrint's datestamp field
- Updated
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2021-11-11Created from EPrint's last_modified field