Design, Synthesis, and Hybridisation of Water-Soluble, Peptoid Nucleic Acid Oligomers Tagged with Thymine
作者： Rosa Zarra , Daniela Montesarchio , Cinzia Coppola , Giuseppe Bifulco , Simone Di Micco
关键词: Monomer 、 Nucleobase 、 Nucleic acid 、 Amide 、 Chemistry 、 Oligomer 、 Peptide nucleic acid 、 Stereochemistry 、 Peptoid 、 Thymine
摘要: The preparation of a new class backbone-modified PNA mimetic incorporating thymine is described. Target dipeptoid monomer 21 was synthesised from an N-[2-(thymin-1-yl)ethyl]glycinate ester and properly protected iminodiacetic acid. distinctive structural motif in the backbone acarboxy group, inserted to impart water solubility oligomer. Two achiral oligopeptoid sequences (8-mer 12-mer), characterised by shift amide carbonyl group away nucleobase, were efficiently assembled according solid-phase synthesis protocols. Thermal denaturation studies showed that two homopyrimidine oligopeptoids do not effectively hybridise with complementary DNA RNA or fully synthetic (2,4-diamino)triazin-6-yl-tagged peptoid 22. A possible reason could reside concurrent unfavourable influence anionic N-(carboxymethyl) moieties flexible nucleobase/backbone ethylene linker.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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unisa.it参考文章(47)
Gordon Lowe, Tirayut Vilaivan, Dipeptides bearing nucleobases for the synthesis of novel peptide nucleic acids Journal of The Chemical Society-perkin Transactions 1. pp. 539- 546 ,(1997) , 10.1039/A603696A
Trine Ljungstrøm, Helle Knudsen, Peter E. Nielsen, Cellular uptake of adamantyl conjugated peptide nucleic acids. Bioconjugate Chemistry. ,vol. 10, pp. 965- 972 ,(1999) , 10.1021/BC990053+
Uffe Koppelhus, Peter E. Nielsen, Cellular delivery of peptide nucleic acid (PNA). Advanced Drug Delivery Reviews. ,vol. 55, pp. 267- 280 ,(2003) , 10.1016/S0169-409X(02)00182-5
Eugen Uhlmann, Anusch Peyman, Gerhard Breipohl, David W. Will, PNA: Synthetic Polyamide Nucleic Acids with Unusual Binding Properties Angewandte Chemie International Edition. ,vol. 37, pp. 2796- 2823 ,(1998) , 10.1002/(SICI)1521-3773(19981102)37:20<2796::AID-ANIE2796>3.0.CO;2-K
Scott J. Weiner, Peter A. Kollman, David A. Case, U. Chandra Singh, Caterina Ghio, Guliano Alagona, Salvatore Profeta, Paul Weiner, A NEW FORCE FIELD FOR MOLECULAR MECHANICAL SIMULATION OF NUCLEIC ACIDS AND PROTEINS Journal of the American Chemical Society. ,vol. 106, pp. 765- 784 ,(1984) , 10.1021/JA00315A051
Albert Eschenmoser, Searching for nucleic acid alternatives Chimia. ,vol. 59, pp. 836- 850 ,(2005) , 10.1002/9780470977873.CH1
Peter E Nielsen, Peptide nucleic acid: a versatile tool in genetic diagnostics and molecular biology. Current Opinion in Biotechnology. ,vol. 12, pp. 16- 20 ,(2001) , 10.1016/S0958-1669(00)00170-1
Birgitte Hyrup, Michael Egholm, Ole Buchardt, Peter E. Nielsen, A flexible and positively charged PNA analogue with an ethylene-linker to the nucleobase: Synthesis and hybridization properties Bioorganic & Medicinal Chemistry Letters. ,vol. 6, pp. 1083- 1088 ,(1996) , 10.1016/0960-894X(96)00176-X
Eugen Uhlmann, David W. Will, Gerhard Breipohl, Dietrich Langner, Antonina Ryte, SYNTHESIS AND PROPERTIES OF PNA/DNA CHIMERAS Angewandte Chemie. ,vol. 35, pp. 2632- 2635 ,(1996) , 10.1002/ANIE.199626321
Pernilla Wittung, Johan Kajanus, Katarina Edwards, Peter Nielsen, Bengt Nordén, Bo G Malmström, None, Phospholipid membrane permeability of peptide nucleic acid FEBS Letters. ,vol. 365, pp. 27- 29 ,(1995) , 10.1016/0014-5793(95)00409-3