Synlett 2013; 24(8): 893-897
DOI: 10.1055/s-0032-1318493
synpacts
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Nucleic Acid Polymers with Non-Canonical Nucleobases

Dennis Gillingham*
Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland   Fax: +41(61)2670976   Email: dennis.gillingham@unibas.ch
,
Kiril Tishinov
Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland   Fax: +41(61)2670976   Email: dennis.gillingham@unibas.ch
› Author Affiliations
Further Information

Publication History

Received: 25 January 2013

Accepted after revision: 04 March 2013

Publication Date:
19 March 2013 (online)


Abstract

Understanding and controlling the biology of nucleic acids is partially a challenge in synthetic chemistry: How to selectively manipulate a single subunit in a repeating polymer of near-identical units. Herein we examine approaches to tackle this synthetic challenge and highlight a recent contribution from our group that offers an efficient convergent method based on organometallic catalysis.

 
  • References

    • 1a Wachowius F, Höbartner C. ChemBioChem 2010; 11: 469
    • 1b Fedorova O, Boudvillain M, Kawaoka J, Pyle AM In Handbook of RNA Biochemistry . Wiley-VCH; Weinheim: 2008: 259-293
    • 1c Huntzinger E, Possedko M, Winter F, Moine H, Ehresmann C, Romby P In Handbook of RNA Biochemistry . Wiley-VCH; Weinheim: 2008: 151-171
  • 2 Tishinov K, Schmidt K, Häussinger D, Gillingham DG. Angew. Chem. Int. Ed. 2012; 51: 12000
  • 3 Höbartner C, Wachowius F. Chemical Synthesis of Modified RNA . In The Chemical Biology of Nucleic Acids . John Wiley and Sons; Chichester: 2010: 1-37
  • 4 Sasaki S, Onizuka K, Taniguchi Y. Chem. Soc. Rev. 2011; 40: 5698-5706
  • 5 Sharp PA. Cell 2009; 136: 577
  • 6 Winkler WC, Nahvi A, Roth A, Collins JA, Breaker RR. Nature (London) 2004; 428: 281
  • 7 Seto AG, Kingston RE, Lau NC. Mol. Cell 2007; 26: 603
  • 8 Bartel DP. Cell 2009; 136: 215
  • 9 Nagano T, Fraser P. Cell 2011; 145: 178
    • 10a Kawasaki T, Nagatsugi F, Ali MM, Maeda M, Sugiyama K, Hori K, Sasaki S. J. Org. Chem. 2004; 70: 14
    • 10b Hattori K, Hirohama T, Imoto S, Kusano S, Nagatsugi F. Chem. Commun. 2009; 6463
  • 11 Song C.-X, He C. Acc. Chem. Res. 2011; 44: 709
    • 12a Zhou Q, Rokita SE. Proc. Natl. Acad. Sci. U.S.A. 2003; 100: 15452
    • 12b Liu Y, Rokita SE. Biochemistry 2012; 51: 1020
  • 13 Onizuka K, Taniguchi Y, Sasaki S. Bioconjugate Chem. 2009; 20: 799
    • 14a Dalhoff C, Lukinavicius G, Klimasauskas S, Weinhold E. Nat. Chem. Biol. 2006; 2: 31
    • 14b Tomkuvienė M, Clouet-d’Orval B, Černiauskas I, Weinhold E, Klimašauskas S. Nucleic Acids Res. 2012; 40: 6765
  • 15 Motorin Y, Burhenne J, Teimer R, Koynov K, Willnow S, Weinhold E, Helm M. Nucleic Acids Res. 2011; 39: 1943
  • 16 Peacock H, Kannan A, Beal PA, Burrows CJ. J. Org. Chem. 2011; 76: 7295