The DOI matches its Crossref record; 18 of the 18 references it cites were found in a registry or an index.
Solid Phase Synthesis of Polyamides Containing Imidazole and Pyrrole Amino Acids
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-β-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.
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Citations
Cites
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Sequence-Specific Cleavage of Double Helical DNA by Triple Helix Formation
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Quantitative monitoring of solid-phase peptide synthesis by the ninhydrin reaction
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Peptoids: a modular approach to drug discovery.
Simon, R. J., Kania, R. S., Zuckermann, R. N., Huebner, V. D., Jewell, D. A., Banville, S., Ng, S., Wang, L., Rosenberg, S., & Marlowe, C. K. (1992) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.89.20.9367 · Cited by 953
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CHEMICAL SYNTHESIS OF PEPTIDES AND PROTEINS
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A general and expedient method for the solid-phase synthesis of 1,4-benzodiazepine derivatives
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Cited by
1,10-Phenanthroline: A versatile building block for the construction of ligands for various purposes
Bencini, A., & Lippolis, V. (2010) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2010.04.008 · Cited by 615
DNA minor-groove recognition by small molecules (up to 2000)
Neidle, S. (2001) · Natural Product Reports · doi:10.1039/a705982e · Cited by 494
Imidazole- and imidazolium-containing polymers for biology and material science applications
Anderson, E. B., & Long, T. E. (2010) · Polymer · doi:10.1016/j.polymer.2010.02.006 · Cited by 407
Bailly, C., & Chaires, J. B. (1998) · Bioconjugate Chemistry · doi:10.1021/bc980008m · Cited by 254
Metadata
- Authors
- Baird, E. E., & Dervan, P. B.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1996-01-01
- Volume
- 118
- Issue
- 26
- Pages
- 6141-6146
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2005611394
- Cited by
- 360
- References
- 18
- FWCI
- 7.30
- Type
- journal article
- Language
- en
- Open access
- closed
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- Baird, E. E., & Dervan, P. B. (1996). Solid Phase Synthesis of Polyamides Containing Imidazole and Pyrrole Amino Acids. Journal of the American Chemical Society. https://doi.org/10.1021/ja960720z
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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