Raw Materials for the Synthesis of PI Polyamide to Recognize DNA Sequences

The amino group sides and the carbonyl group sides in PIPs (pyrrole-imidazole (Py-Im) polyamides) face each other in antiparallel to form Py/Py or Py/Im pairs. They recognize specific DNA base pairs via hydrogen bonds, enter the minor-groove of the DNA double helix to bind sequence-selectively. By changing the sequence of Py and Im, it is possible to design and bind to any DNA base sequences.^1-4) Both 1-methyl-pyrrole (1, 2) and 1-methyl-imidazole (3, 4) monomers with Boc- or Fmoc-protected amino groups have been used as raw materials for the synthesis of PIPs. In addition, the PyIm block (5), which is difficult to lengthen by solid-phase synthesis, is also available.^5-7)

Related Products

B6351

4-(Boc-amino)-1-methyl-1H-pyrrole-2-carboxylic Acid (= Boc-Py-OH)

F1314

4-(Fmoc-amino)-1-methyl-1H-pyrrole-2-carboxylic Acid (= Fmoc-Py-OH)

B6350

4-(Boc-amino)-1-methyl-1H-imidazole-2-carboxylic Acid (= Boc-Im-OH)

F1313

4-(Fmoc-amino)-1-methyl-1H-imidazole-2-carboxylic Acid (= Fmoc-Im-OH)

F1315

Fmoc-PyIm-COOH

B4291

N-Boc-4-aminobutyric Acid

F0911

N-Fmoc-4-aminobutyric Acid

References

• 1) Recognition of DNA by designed ligands at subnanomolar concentrations
  • J. W. Trauger, E. E. Baird, P. B. Dervan, Nature 1996, 382, 559.
• 2) Extension of Sequence-Specific Recognition in the Minor Groove of DNA by Pyrrole−Imidazole Polyamides to 9−13 Base Pairs
  • J. W. Trauger, E. E. Baird, M. Mrksich, P. B. Dervan, J. Am. Chem. Soc. 1996, 118, 6160.
• 3) Solid Phase Synthesis of Polyamides Containing Imidazole and Pyrrole Amino Acids
  • E. E. Baird, P. B. Dervan, J. Am. Chem. Soc. 1996, 118, 6141.
• 4) Chemical Approaches to the Development of Artificial Transcription Factors Based on Pyrrole-Imidazole Polyamides
  • T. Hidaka, H. Sugiyama, Chem. Rec. 2021, 21, 1374.
• 5) Rapid solid-Phase synthesis of DNA-Binding pyrrole-Imidazole polyamides
  • P. O. Krutzik, A. R. Chamberlin, Bioorg. Med. Chem. Lett. 2002, 12, 2129.
• 6) Highly Efficient Synthesis of DNA-Binding Hairpin Polyamides via the Use of a New Triphosgene Coupling Strategy
  • W. S. Stephen, J. G. Ruggero Dondi, G. A. Burley, Org. Lett. 2009, 11, 3910.
• 7) Fully Automated Synthesis of DNA-Binding Py-Im Polyamides Using a Triphosgene Coupling Strategy
  • L. Fang, G. Yao, Z. Pan, C. Wu, H. S. Wang, G. A. Burley, W. Su, Org. Lett. 2015, 17, 158.

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