- Synthesis of an Fmoc N-methyl 1H-pyrrole amino acid pentafluoro-phenol ester
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A derivative of 4-amino-N-methyl 1H-pyrrole-2-carboxylic acid was synthesized which is suitable for automated solid phase Fmoc protocols.
- Koenig, Burkhard,Roedel, Martin
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- An Fmoc solid-phase approach to linear polypyrrole-peptide conjugates
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A practical method for the synthesis of medium-sized peptides incorporating several N-methylpyrrole units is described. These peptides might prove useful as novel sequence-specific DNA binders.
- Vazquez, Eugenio,Caamano, Ana M.,Castedo, Luis,Mascarenas, Jose L.
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- 4-Methyltrityl-Protected Pyrrole and Imidazole Building Blocks for Solid Phase Synthesis of DNA-Binding Polyamides
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DNA-binding polyamides are synthetic oligomers of pyrrole/imidazole units with high specificity and affinity for double-stranded DNA. To increase their synthetic diversity, we report a mild methodology based on 4-methyltrityl (Mtt) solid phase peptide synthesis (SPPS), whose building blocks are more accessible than the standard Fmoc and Boc SPPS ones. We demonstrate the robustness of the approach by preparing and studying a hairpin with all precursors. Importantly, our strategy is orthogonal and compatible with sensitive molecules and could be readily automated.
- Heinrich, Benedikt,Vázquez, Olalla
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supporting information
p. 533 - 536
(2020/01/31)
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- Series of oligopolyamide containing N-methylpyrrole and N-methylimidazole and synthesis method thereof
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The invention discloses a series of oligopolyamide DNA minor groove ligand compounds containing N-methylpyrrole and N-methylimidazole and a synthesis method thereof. The synthesis method provided by the invention adopts a five-membered heterocyclic compound and a derivative thereof as the raw materials, and carries out a series of reactions like acylation, nitration, hydrogenation, condensation, hydrolysis and the like to synthesize the target product. The synthesis method provided by the invention is also applicable to synthesis of polyamide. The synthetic process adopted by the method provided by the invention has the characteristics of simple operation and high yield, and is suitable for industrial scale production. The oligopolyamide DNA minor groove ligand compounds containing N-methylpyrrole and N-methylimidazole provided by the invention have structural formulas shown as formula I and formula II in the specification.
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- Method of the solid phase synhesis of pyrrole-imidazole polyamide
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It is intended to provide a method of producing a pyrrole-imidazole polyamide whereby a longer pyrrole-imidazole polyamide can be conveniently synthesized and a peptide (protein) can be easily transferred. According to this method, a pyrrole-imidazole polyamide having a carboxylate group which can be excised from a solid phase carrier at its end, makes it possible to directly transfer various functional groups and can exactly distinguish DNA sequences can be efficiently produced. A method of synthesizing a pyrrole-imidazole polyamide characterized by performing automatic synthesis by the solid phase Fmoc method with the used of a peptide synthesizer; a pyrrole-imidazole polyamide having a carboxyl group at its end obtained by this method; a pyrrole-imidazole polyamide having a DNA alkylation agent transferred into the carboxyl group at the end of the above-described pyrrole-imidazole polyamide; and a sequence-specific DNA alkylation method characterized by using the above compound.
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- Fmoc solid phase synthesis of polyamides containing pyrrole and imidazole amino acids
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Matrix presented 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.
- Wurtz, Nicholas R.,Turner, James M.,Baird, Eldon E.,Dervan, Peter B.
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p. 1201 - 1203
(2007/10/03)
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