Highly Efficient Synthesis of DNA-Binding Polyamides Using a Convergent Fragment-Based Approach

Fallows, Andrew J.; Singh, Ishwar; Dondi, Ruggero; Cullis, Paul M.; Burley, Glenn A.

doi:10.1021/ol502203y

Cited by 11 publications

(2 citation statements)

References 39 publications

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“…10 However, the following intramolecular nucleophilic attack by alanine amine did not occur possibly due to the steric hindrance of the C-terminal MeIle residue. Direct aminolysis of resinbound peptide 2 under air at elevated temperatures (55 and 90 °C) 19 did not provide any of the cyclized product, either. Consequently, the solid-phase macrocyclization approach had to be adjusted and a solution-phase cyclization was conducted (Scheme 4).…”

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confidence: 91%

Efficient Synthesis and Stereochemical Revision of Coibamide A

Yao

Zhang

et al. 2015

J. Am. Chem. Soc.

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Coibamide A is a highly potent antiproliferative cyclodepsipeptide originally isolated from a Panamanian marine cyanobacterium. Herein we report an efficient solid-phase strategy for assembly of highly N-methylated cyclodepsipeptides, which is invaluable in generating coibamide A derivatives for structure-activity relationship studies. As a consequence of our synthetic studies, two stereochemical assignments of coibamide A were revised and the total synthesis of this natural compound was achieved for the first time.

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confidence: 91%

Efficient Synthesis and Stereochemical Revision of Coibamide A

Yao

Zhang

et al. 2015

J. Am. Chem. Soc.

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“…Over the past two decades, much attention has been devoted to the total synthesis of Py-Im polyamides . The syntheses of these molecules are challenging as a consequence of the low inherent nucleophilicity of the immobilized aromatic amine.…”

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confidence: 99%

Fully Automated Synthesis of DNA-Binding Py-Im Polyamides Using a Triphosgene Coupling Strategy

et al. 2014

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The fully automated solid-phase synthetic strategy of hairpin pyrrole-imidazole polyamides is described. A key advance is the development of methodology for the application of triphosgene as a coupling agent in the automated synthesis of hairpin polyamides without racemization. This automated methodology is compatible with all the typical building blocks, enabling the facile synthesis of polyamide libraries in good yield (9-15%) and crude purity.

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Pyrrole‐Imidazole Polyamides: Manual Solid‐Phase Synthesis

Pauff

Fallows

Mackay

et al. 2015

CP Nucleic Acid Chemistry

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Pyrrole-imidazole polyamides (PAs) are a family of DNA-binding peptides that bind in the minor groove of double-stranded DNA (dsDNA) in a sequence-selective, programmable fashion. This protocol describes a detailed manual procedure for the solid-phase synthesis of this family of compounds. The protocol entails solution-phase synthesis of the Boc-protected pyrrole (Py) and imidazole (Im) carboxylic acid building blocks. This unit also describes the importance of choosing the appropriate condensing agent to form the amide linkages between each building block. Finally, a monomeric coupling protocol and a fragment-based approach are described that delivers PAs in 13% to 30% yield in 8 days.

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Highly Efficient Synthesis of DNA-Binding Polyamides Using a Convergent Fragment-Based Approach

Cited by 11 publications

References 39 publications

Efficient Synthesis and Stereochemical Revision of Coibamide A

Efficient Synthesis and Stereochemical Revision of Coibamide A

Fully Automated Synthesis of DNA-Binding Py-Im Polyamides Using a Triphosgene Coupling Strategy

Pyrrole‐Imidazole Polyamides: Manual Solid‐Phase Synthesis

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