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Synlett 2011(14): 1956-1964  
DOI: 10.1055/s-0030-1261177
SYNPACTS
© Georg Thieme Verlag Stuttgart ˙ New York

The Origins of Nucleotides

Matthew W. Powner*a, John D. Sutherlandb, Jack W. Szostaka
Howard Hughes Medical Institute, and Department of Molecular Biology and Center for Computational and Integrative Biology, Massachusetts General Hospital, 185 Cambridge Street, Boston, Massachusetts 02114, USA
Fax: +1(617)6433328; e-Mail: powner@molbio.mgh.harvard.edu;
MRC Laboratory of Molecular Biology, Hills Road, Cambridge, CB2 0QH, UK
Further Information

Publication History

Received 18 April 2011
Publication Date:
10 August 2011 (online)

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Abstract

The origins of life represent one of the most fundamental chemical questions being addressed by modern science. One of the longstanding mysteries of this field is what series of chemical reactions could lead to the molecular biologists dream; a pool of homochiral nucleotides? Here we summarize those results we consider to be historically important and outline our recently published research aimed at understanding the chemoselective origins of the ­canonical ribonucleotides.

1 Introduction

1.1 Nucleotides: What’s the Problem?

2 Synthesis of Activated Pyrimidines

2.1 Pyrimidine Elaboration by Cyanovinylation

2.2 Photochemical Epimerization and Cytidine to Uridine
Conversion

2.3 Urea-Mediated Phosphoryl Transfer and Intramolecular
Rearrangement

2.4 Pyrimidine Photosanitization

3 Chemoselective Purine Glycosylation

4 Future Scope for Investigation

5 Conclusion

Key words

nucleotides - chemoselectivity - multicomponent reactions - rearrangement - photochemistry

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