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DNA and RNA Pyrimidine Nucleobase Alkylation at the Carbon-5 Position

  • Yuri MotorinEmail author
  • Salifu Seidu-Larry
  • Mark HelmEmail author
Chapter
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 945)

Abstract

The carbon 5 of pyrimidine nucleobases is a privileged position in terms of nucleoside modification in both DNA and RNA. The simplest modification of uridine at this position is methylation leading to thymine. Thymine is an integral part of the standard nucleobase repertoire of DNA that is synthesized at the nucleotide level. However, it also occurs in RNA, where it is synthesized posttranscriptionally at the polynucleotide level. The cytidine analogue 5-methylcytidine also occurs in both DNA and RNA, but is introduced at the polynucleotide level in both cases. The same applies to a plethora of additional derivatives found in nature, resulting either from a direct modification of the 5-position by electrophiles or by further derivatization of the 5-methylpyrimidines. Here, we review the structural diversity of these modified bases, the variety of cofactors that serve as carbon donors, and the common principles shared by enzymatic mechanisms generating them.

Keywords

Michael Addition Pyrimidine Ring Enzymatic Mechanism Hydride Transfer Pyrimidine Nucleoside 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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© Springer International Publishing Switzerland 2016

Authors and Affiliations

  1. 1.IMoPA UMR7365 CNRS-ULBioPole de l’Université de LorraineVandoeuvre-les-NancyFrance
  2. 2.Department of BiochemistryUniversity of Cape Coast, College of Agriculture and Natural Sciences, School of Biological SciencesCape CoastGhana
  3. 3.Institute of Pharmacy and BiochemistryJohannes Gutenberg University MainzMainzGermany

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