caa a22 4500 378921584 CHVBK 20180305123606.0 cr unu---uuuuu 161128e20040101xx s 000 0 eng 10.1351/pac200476071591 doi (NATIONALLICENCE)gruyter-10.1351/pac200476071591 Chemistry for the synthesis of nucleobase-modified peptide nucleic acid [Elektronische Daten] [R. H. E. Hudson, R. D. Viirre, Y. H. Liu, F. Wojciechowski, A. K. Dambenieks] Peptide nucleic acid (PNA) presents a versatile scaffold for chemical modifications that may benefit its solubility and hybridization properties, conjugation chemistry, cell membrane permeability, and so forth. We have employed straightforward chemical methods for the synthesis of PNA monomers containing C5-or C6-modified pyrimidines.The C5-modified pyrimidines are based on 5-hydroxymethyl-uracil or cytosine, or are achieved by cross-coupling from the 5-iodonucleobase derivatives, while C6 modifications are accessed from 6-carboxyuracil (orotic acid). We have also developed an on-resin activation/conversion of uracil-containing PNA oligomers to N4-cytosine-containing derivatives. © 2013 Walter de Gruyter GmbH, Berlin/Boston Hudson R. H. E. Department of Chemistry, The University of Western Ontario, London, Ontario N6A 5B7, Canada aut Viirre R. D. Department of Chemistry, The University of Western Ontario, London, Ontario N6A 5B7, Canada aut Liu Y. H. Department of Chemistry, The University of Western Ontario, London, Ontario N6A 5B7, Canada aut Wojciechowski F. Department of Chemistry, The University of Western Ontario, London, Ontario N6A 5B7, Canada aut Dambenieks A. K. Department of Chemistry, The University of Western Ontario, London, Ontario N6A 5B7, Canada aut Pure and Applied Chemistry De Gruyter 76/7-8(2004-01-01), 1591-1598 0033-4545 76:7-8<1591 2004 76 pac https://doi.org/10.1351/pac200476071591 text/html Onlinezugriff via DOI 1 research article jats NATIONALLICENCE 856 40 https://doi.org/10.1351/pac200476071591 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Hudson R. H. E. Department of Chemistry, The University of Western Ontario, London, Ontario N6A 5B7, Canada aut NATIONALLICENCE 700 1- Viirre R. D. Department of Chemistry, The University of Western Ontario, London, Ontario N6A 5B7, Canada aut NATIONALLICENCE 700 1- Liu Y. H. Department of Chemistry, The University of Western Ontario, London, Ontario N6A 5B7, Canada aut NATIONALLICENCE 700 1- Wojciechowski F. Department of Chemistry, The University of Western Ontario, London, Ontario N6A 5B7, Canada aut NATIONALLICENCE 700 1- Dambenieks A. K. Department of Chemistry, The University of Western Ontario, London, Ontario N6A 5B7, Canada aut NATIONALLICENCE 773 0- Pure and Applied Chemistry De Gruyter 76/7-8(2004-01-01), 1591-1598 0033-4545 76:7-8<1591 2004 76 pac CC0 http://creativecommons.org/publicdomain/zero/1.0 nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-gruyter