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Synthesis 2002(3): 0301-0314
DOI: 10.1055/s-2002-20030
REVIEW
© Georg Thieme Verlag Stuttgart · New York

Chemical Synthesis of ¹³ C and ¹5 N Labeled Nucleosides

Irene M. Lagoja, Piet Herdewijn*
Katholieke Universiteit Leuven, Laboratory of Medicinal Chemistry Rega Institute for Medical Research, Minderbroedersstraat 10, 3000 Leuven, Belgium
Fax: +32(16)337340; e-Mail: Irene.Lagoja@rega.kuleuven.ac.be; e-Mail: Piet.Herdewijn@rega.kuleuven.ac.be;
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Publikationsverlauf

Received 8 October 2001
Publikationsdatum:
28. Juli 2004 (online)

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Abstract

The chemical synthesis of 13C and 15N labeled nucleosides for site-specific incorporation in RNA or DNA oligonucleotides is herein reviewed. The review covers the following aspects: 1: single- and multiple site chemical 13C and/or 15N labeling of purine bases, 2: single- and multiple site chemical 13C and/or 15N labeling of pyrimidine bases, 3: single- and multiple site chemical 13C labeling of the sugar residues.

  • 1 Introduction

  • 2 Enzymatic Synthesis of 13C/15N Labeled Bases and Nucleic Acids

  • 3 Synthesis of 13C/15N Labeled Purines

  • 3.1 Carbon and Nitrogen Labeling at the Level of the Bases

  • 3.2 Carbon and Nitrogen Labeling at the Nucleoside/Nucleotide Level

  • 4 Synthesis of 13C/15N Labeled Pyrimidines

  • 4.1 Synthesis of 13C/15N Labeled Uracil and Thymidine

  • 4.2 Synthesis of 13C/15N Labeled Cytosine

  • 5 13C Labeling of Sugars

  • 5.1 Uniformly 13C5 Labeling of Ribose

  • 5.2 Selective Carbon Labeling at the Sugar Moiety

  • 6 Conclusions

Key words

chemical synthesis - labeled nucleosides - 13C/15N labeling of nucleic bases - uniformly 13C labeling of sugars - selective 13C labeling of sugars