Nucleosides and Nucleotides

Nucleosides and nucleotides are fundamental components of nucleic acids, such as DNA and RNA, and they play crucial roles in various cellular processes. These molecules are composed of a combination of a nitrogenous base, a pentose sugar, and one or more phosphate groups They are key to maintaining and transferring genetic information, functioning as signaling molecules, and additionally play an important role in biological energy storage. Below more detail is given into their biological function.

Genetic Information: Nucleotides are the units that make up DNA and RNA, and they carry the genetic information that determines the characteristics and functions of living organisms. In DNA, the sequence of nucleotides encodes the instructions for building and maintaining an organism, and it can be passed on from one generation to the next. RNA plays a role in gene expression and protein synthesis.

Energy Carriers: Nucleotides like ATP (adenosine triphosphate) and GTP (guanosine triphosphate) serve as high-energy molecules that power various cellular processes. They store and transfer energy within the cell and are crucial for metabolic reactions.

Cell Signaling: Certain nucleotides and nucleosides, like cAMP (cyclic adenosine monophosphate) and cGMP (cyclic guanosine monophosphate), are involved in cell signaling pathways. They transmit signals from the cell surface to the interior, regulating various cellular responses.

Enzyme Cofactors: Nucleotides can serve as cofactors for enzymes, facilitating their catalytic activities. For example, NAD+ (nicotinamide adenine dinucleotide) and FAD (flavin adenine dinucleotide) are coenzymes that play essential roles in redox reactions.

Nucleosides and nucleotides 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] The structure and difference between nucleosides and nucleotidesis delineated in Figure 1.

Nucleosides and nucleotides basic structures Symeres
Figure 1. The basic structures of nucleosides and nucleotides.

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.

Examples of nucleotides previously synthesized at Symeres.
Figure 2. Examples of nucleotides previously synthesized at Symeres.

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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

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