Nucleosides and nucleotides are key to maintaining and transferring genetic information, functioning as signaling molecules, and playing an important role in biological energy storage. They can be divided into two main classes: purines, which include adenine and guanine, and pyrimidines, which include cytosine, uracil, and thymine. These unique compounds and their interactions serve as the foundation of DNA and RNA molecules.[1]
Synthesis of Nucleosides and Nucleotides
Symeres has a strong track record, over many years, for the challenging synthesis and purification of nucleosides and nucleotides. Factors such as the presence of polar and charged functional groups, instability of the pyrophosphate bond, and complex and time-consuming purifications make nucleoside and nucleotide chemistry a specialized field that requires significant experience, despite the substantial amount of research published in the area.[2],[3] Methods for efficient ways to prepare nucleosides and nucleotides have been extensively explored. In chemical synthesis, two different approaches can be considered: solution-phase or solid-support synthesis. Both protected and unprotected starting materials can be employed, depending on the type of reagents chosen. Purity determination and purification of nucleosides and nucleotides bring a number of challenges. We apply HPLC methods with specific columns for polar compounds to monitor reaction progress and determine purity. Purification methods adopted include preparative HPLC, reverse-phase chromatography, ion-exchange chromatography, or using polystyrene or Sephadex resins.
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[1] L. W. Jansonet al., The Big Picture: Medical Biochemistry, Chapter 4: Nucleosides, Nucleotides, DNA, and RNA, 2018
[2] B. Roy et al., Chem. Rev. 2016, 14 , 7854–7897 DOI: https://doi.org/10.1021/acs.chemrev.6b00174
[3] G.K. Wagner et al., Nat. Prod. Rep. 2009, 26 , 1172–1194 DOI: https://doi.org/10.1039/B909621N
