Synthesis of Nucleic Acid Polymers with Non-Canonical Nucleobases

Dennis Gillingham; Kiril Tishinov

doi:10.1055/s-0032-1318493

Synlett, Table of Contents

Synlett 2013; 24(8): 893-897
DOI: 10.1055/s-0032-1318493

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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

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Abstract

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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.

Key words

bioorganic chemistry - carbenoids - DNA - nucleobases - catalysis

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References

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