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Peptidosteroid tweezers revisited: DNA binding through an optimised design

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Abstract
A dipodal peptidosteroid based on a deoxycholic acid scaffold was designed as a transcription factor model to study, and ultimately interfere in, selective protein–DNA interactions. In this paper, the selective binding of such a dipodal peptidosteroid to its DNA binding site is described for the first time, thus proving the concept and confirming the potential of the design. To achieve this, two 25-mer peptides were synthesized in parallel and in close proximity on a rigid amphiphilic scaffold, attached by flexible linkers. Peptide aggregation complicated the synthesis under conventional conditions to such an extent that optimization and the use of microwave assistance were required for a successful synthesis. As such, this synthesis is a good model to showcase the beneficial effects of microwave assistance in peptide synthesis.
Keywords
DNA recognition, Protein ­models, Peptides, Microwave chemistry, Steroids, SOLID-PHASE SYNTHESIS, DIFFICULT PEPTIDE SEQUENCES, TRANSCRIPTION FACTORS, CHOLIC-ACID, MICROWAVE IRRADIATION, CHEMICAL-SYNTHESIS, ORGANIC-SYNTHESIS, STEROID SCAFFOLD, DEOXYCHOLIC-ACID, BILE-ACID

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Citation

Please use this url to cite or link to this publication:

Chicago
Carrette, Lieselot, Takashi Morii, and Annemieke Madder. 2014. “Peptidosteroid Tweezers Revisited: DNA Binding Through an Optimised Design.” European Journal of Organic Chemistry (14): 2883–2891.
APA
Carrette, L., Morii, T., & Madder, A. (2014). Peptidosteroid tweezers revisited: DNA binding through an optimised design. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (14), 2883–2891.
Vancouver
1.
Carrette L, Morii T, Madder A. Peptidosteroid tweezers revisited: DNA binding through an optimised design. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2014;(14):2883–91.
MLA
Carrette, Lieselot, Takashi Morii, and Annemieke Madder. “Peptidosteroid Tweezers Revisited: DNA Binding Through an Optimised Design.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 14 (2014): 2883–2891. Print.
@article{4376154,
  abstract     = {A dipodal peptidosteroid based on a deoxycholic acid scaffold was designed as a transcription factor model to study, and ultimately interfere in, selective protein--DNA interactions. In this paper, the selective binding of such a dipodal peptidosteroid to its DNA binding site is described for the first time, thus proving the concept and confirming the potential of the design. To achieve this, two 25-mer peptides were synthesized in parallel and in close proximity on a rigid amphiphilic scaffold, attached by flexible linkers. Peptide aggregation complicated the synthesis under conventional conditions to such an extent that optimization and the use of microwave assistance were required for a successful synthesis. As such, this synthesis is a good model to showcase the beneficial effects of microwave assistance in peptide synthesis.},
  author       = {Carrette, Lieselot and Morii, Takashi and Madder, Annemieke},
  issn         = {1434-193X},
  journal      = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY},
  language     = {eng},
  number       = {14},
  pages        = {2883--2891},
  title        = {Peptidosteroid tweezers revisited: DNA binding through an optimised design},
  url          = {http://dx.doi.org/10.1002/ejoc.201301854},
  year         = {2014},
}

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