Dipeptides bearing nucleobases for the synthesis of novel peptide nucleic acids

被引:25
|
作者
Lowe, G
Vilaivan, T
机构
[1] Dyson Perrins Laboratory, Oxford University, Oxford OX1 3QY, South Parks Road
关键词
D O I
10.1039/a603699f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three stereoisomers (cis-L, trans-D and cis-D) of N-Fmoc-glycyl-4-(thymin-1-yl)proline and their pentafluorophenyl esters have been prepared for use in the synthesis of novel peptide nucleic acids. In addition, N-Fmoc-glycyl-4(N-6-benzoyladenin-9-yl)proline, N-Fmoc-glycyl-4-(N-4-benzoylcytosin-1-yl)proline and N-Fmoc-glycyl-4-(N-2-isobutyrylguanin-9-yl)proline and their pentafluorophenyl esters of the cis-D series have been synthesized.
引用
收藏
页码:547 / 554
页数:8
相关论文
共 50 条
  • [41] Novel Rath peptide for intracellular delivery of protein and nucleic acids
    Bais, Manish V.
    Kumar, Satish
    Tiwari, Ashok K.
    Kataria, Ranjit S.
    Nagaleekar, Viswas K.
    Shrivastava, Sameer
    Chindera, Kantaraja
    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2008, 370 (01) : 27 - 32
  • [42] Comparison of novel delivery systems for antisense peptide nucleic acids
    Chiarantini, L
    Cerasi, A
    Fraternale, A
    Millo, E
    Benatti, U
    Sparnacci, K
    Laus, M
    Ballestri, M
    Tondelli, L
    JOURNAL OF CONTROLLED RELEASE, 2005, 109 (1-3) : 24 - 36
  • [43] Quantum Mechanical Studies on the Photophysics and the Photochemistry of Nucleic Acids and Nucleobases
    Improta, Roberto
    Santoro, Fabrizio
    Blancafort, Lluis
    CHEMICAL REVIEWS, 2016, 116 (06) : 3540 - 3593
  • [44] Peptide nucleic acids and their phosphonate analogues: Synthesis and hybridization properties
    Efimov, VA
    Buryakova, AA
    Choob, MV
    Chakhmakhcheva, OG
    BIOORGANICHESKAYA KHIMIYA, 1998, 24 (09): : 696 - 709
  • [45] Convergent synthesis of peptide nucleic acids by native chemical Ligation
    Dose, C
    Seitz, O
    ORGANIC LETTERS, 2005, 7 (20) : 4365 - 4368
  • [46] Synthesis of 2-Aminopyridine-Modified Peptide Nucleic Acids
    Kumpina, Ilze
    Baskevics, Vladislavs
    Walby, Grant D.
    Tessier, Brandon R.
    Saei, Sara Farshineh
    Ryan, Christopher A.
    Mackay, James A.
    Katkevics, Martins
    Rozners, Eriks
    SYNLETT, 2024, 35 (06) : 649 - 653
  • [47] Synthesis, properties and functions of peptide nucleic acids (PNA) and their derivatives
    Iwase, R
    Murakami, A
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2002, 60 (12) : 1179 - 1189
  • [48] Synthesis of chiral peptide nucleic acids using Fmoc chemistry
    Wu, Y
    Xu, JC
    TETRAHEDRON, 2001, 57 (38) : 8107 - 8113
  • [49] Ionic liquid mediated synthesis of peptide nucleic acids dimers
    Poletti, Laura
    Giannini, Clelia
    TETRAHEDRON, 2013, 69 (07) : 1940 - 1944
  • [50] Peptide Nucleic Acids: Recent Developments in the Synthesis and Backbone Modifications
    Singh, Gurpreet
    Monga, Vikramdeep
    BIOORGANIC CHEMISTRY, 2023, 141