Chemical Synthesis of ¹³C and ¹5N Labeled Nucleosides

Irene M. Lagoja; Piet Herdewijn

doi:10.1055/s-2002-20030

REVIEW

Chemical Synthesis of ^¹³C and ^¹5N 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;

Abstract

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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

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Chemical Synthesis of ¹³ C and ¹5 N Labeled Nucleosides

Chemical Synthesis of ^¹³C and ^¹5N Labeled Nucleosides