Orthogonal Synthesis of Xeno Nucleic Acids

被引:7
|
作者
Fiers, Guillaume [1 ]
Chouikhi, Dalila [1 ,2 ]
Oswald, Laurence [1 ]
Al Ouahabi, Abdelaziz [1 ]
Chan-Seng, Delphine [1 ]
Charles, Laurence [3 ]
Lutz, Jean-Francois [1 ]
机构
[1] Inst Charles Sadron, Precis Macromol Chem Grp, 23 Rue Loess,BP84047, F-67034 Strasbourg, France
[2] Univ Abou Bekr Belkaid Tlemcen, Lab Catalyse & Synth Chim Organ, BP 119 Pole Imama Bat B, Tilimsen 13000, Algeria
[3] Aix Marseille Univ, Inst Rad Chem, CNRS, UMR 7273, Marseille, France
关键词
iterative chemistry; nucleic acids; orthogonal synthesis; sequence-controlled polymers; solid-phase synthesis; SOLID-PHASE SYNTHESIS; INFORMATION-CONTAINING MACROMOLECULES; DNA-TEMPLATED POLYMERIZATION; ENCODED OLIGOMERS; PEPTIDE BACKBONE; GENETIC POLYMERS; CLICK CHEMISTRY; PNA; SEGMENTS; PEPTOIDS;
D O I
10.1002/chem.201604386
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Sequence-defined peptide triazole nucleic acids (PTzNA) were synthesized by means of a solid-phase orthogonal "AB + CD" iterative strategy. In this approach, AB and CD building blocks containing carboxylic acid (A), azide (B), alkyne (C), and primary amine (D) functions are assembled together by successive copper-catalyzed azide-alkyne cycloaddition (CuAAC) and acid-amine coupling steps. Different PTzNA genetic sequences were prepared using a library of eight building blocks (i.e., four AB and four CD building blocks).
引用
收藏
页码:17945 / 17948
页数:4
相关论文
共 50 条
  • [31] Clickable Nucleic Acids: Sequence- Controlled Periodic Copolymer/ Oligomer Synthesis by Orthogonal Thiol-X Reactions
    Xi, Weixian
    Pattanayak, Sankha
    Wang, Chen
    Fairbanks, Benjamin
    Gong, Tao
    Wagner, Justine
    Kloxin, Christopher J.
    Bowman, Christopher N.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (48) : 14462 - 14467
  • [32] Synthesis of Several Types of Bridged Nucleic Acids
    Rahman, S. M. Abdur
    Imanishi, Takeshi
    Obika, Satoshi
    CHEMISTRY LETTERS, 2009, 38 (06) : 512 - 517
  • [33] SYNTHESIS OF NUCLEIC ACIDS IN ESCHERICHIA-COLI
    SIMINOVITCH, L
    GRAHAM, AF
    CANADIAN JOURNAL OF MICROBIOLOGY, 1955, 1 (09) : 721 - 732
  • [34] Nucleic acids delivering nucleic acids
    Catuogno, Silvia
    Esposito, Carla Lucia
    Condorelli, Gerolama
    de Franciscis, Vittorio
    ADVANCED DRUG DELIVERY REVIEWS, 2018, 134 : 79 - 93
  • [35] A new method for the synthesis of peptide nucleic acids
    Wexselblatt, E.
    Yavin, E.
    Katzhendler, J.
    Vaksman, O.
    Reich, R.
    CHEMISTRY OF NUCLEIC ACID COMPONENTS, 2008, 10 : 471 - 472
  • [36] Synthesis of phosphonate analogues of peptide nucleic acids
    Efimov, VA
    Choob, MV
    Kalinkina, AL
    Chakhmakhcheva, OG
    Stromberg, R
    VanDerLaan, AC
    Meeuwenoord, NJ
    KuylYeheskiely, E
    VanBoom, JH
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1996, 61 : S262 - S264
  • [37] Antimicrobials that affect the synthesis and conformation of nucleic acids
    Cambau, E.
    Guillard, T.
    REVUE SCIENTIFIQUE ET TECHNIQUE-OFFICE INTERNATIONAL DES EPIZOOTIES, 2012, 31 (01): : 65 - 87
  • [38] Optimizing the automated synthesis of peptide nucleic acids
    Aguiar, Luisa
    Zitterbart, Robert
    Muthyala, Manoj Kumar
    Ludtke, Stephan
    JOURNAL OF PEPTIDE SCIENCE, 2024, 30
  • [39] ON PARTICIPATION OF NUCLEIC ACIDS IN PROCESS OF CHLOROPHYLL SYNTHESIS
    BERIDZE, TG
    ODINTSOVA, MS
    CHERKASHINA, NA
    SISAKYAN, NM
    DOKLADY AKADEMII NAUK SSSR, 1966, 166 (06): : 1454 - +
  • [40] ACTION OF INHIBITORS OF NUCLEIC ACIDS SYNTHESIS ON EUGLENA
    EBRINGER, L
    EXPERIENTIA, 1971, 27 (05): : 586 - +