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Difference Between Adenine and Adenosine

Adenine

Adenine

In the study of chemistry, chemicals are grouped according to structural similarities. This depends on several factors, such as base elements, the type of bonds that hold elements together, and other attached compounds. These are the fundamental principles behind the nomenclature of various chemicals. Despite the different nomenclatures, two chemicals may sound alike because they can have similar components. This is seen in chemicals like adenine and adenosine, which may be confused with each other. These chemicals have structural and functional differences which will be discussed in this article.

Adenine

Adenine is a purine derivative that forms as the base component of the ubiquitously encountered nucleic acids, deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). This chemical was first isolated from the acid hydrolysate of a protein called nuclein, which was found in beef pancreas in 1885. Purines are composed of a five-membered imidazole ring, combined with a six-membered pyrimidine ring. Purines are further classified according to the number of amino groups and oxy groups that are integrated into their basic structural component. Adenine contains six amino groups, and is referred to as the 6-amino purine. The molecular formula of adenine is C5H5N5. Adenine can be chemically synthesized from heating a mixture of ammonia, water, and hydrogen cyanide for many days. Another way of producing adenine is through irradiating a dilute hydrogen cyanide solution.

Adenine functions as one of the nitrogenous bases for nucleic acids. Nucleic acids, DNA and RNA, are the structural component of human and animal genetic material. Adenine, also, serves as a precursor for adenosine, which we will discuss in the next section of this article. Derivatives of adenine, also, has a therapeutic significance. These derivatives that bear the acyclic nucleoside phosphonates were found to have anti-viral and cytostatic activity. At present, these chemicals are ingredients for drugs that are being used for the treatment of viral infections from Human Immunodeficiency Virus, Hepatitis B and C Viruses, Cytomegalovirus, and Epstein-Barr virus.

Adenosine

Adenosine is a purine nuceloside, which contains adenine as its nucleobase. A nucleoside is a compound that contains a nucleobase that is attached to a sugar molecule through a glycosidic bond. In adenosine, the sugar moiety is ribose. Its chemical formula is C10H13N5O4.Compared to adenine, adenosine is not a component of genetic material. Rather, it is important in various physiologic processes of the body because it serves as a derivative of an important energy source: adenosine triphosphate. As evidence by its nomenclature, adenosine triphosphate contains three phosphate molecules. This is an important chemical for cellular respiration and metabolism.

Adenosine, in itself, is a neurotransmitter which serves various physiologic functions. If it binds to smooth muscles of blood vessels, it causes the blood vessel to relax, allowing blood to flow properly. This bears significance in the study of medicine because in the heart, adenosine binds to receptors that activates the signal transduction pathway. This causes an effect in the conduction pathways of the heart. This is the reason why adenosine is used as an emergency medication in certain cases of life-threatening arrhythmias.

Summary
Chemical compounds are named after their structural components. Chemicals with similar components, as seen in adenine and adenosine, can be confusing because of similar sounding names. However, these chemicals have different structures and functions. Adenine is a purine derivative which is composed of six amino groups combined with a five-membered imidazole ring and fused to a six-membered pyrimidine ring. Adenine is the precursor of adenosine, which is synthesized by the attachment of a sugar moiety through a glycosidic bond. Both adenine and adenosine have important functions in the human body. Adenine is a component of genetic material, while adenosine functions as a neurotransmitter and serves as a precursor for adenosine triphosphate, which is a main energy source for cells. Adenine and adenosine, also, has therapeutic functions. Adenine derivatives are pharmaceutically manufactured as anti-virals, while adenosine is a pharmacologic agent that treats conduction defects of the heart.

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References :


[0]Clercq, E. D. (2011). The clinical potential of the acyclic (and cyclic) nucleoside phosphonates. The magic of the phosphonate bond. Biochemical Pharmacology, 82(2), 99-109. doi:10.1016/j.bcp.2011.03.027

[1]Dewick, P. M. (2006). Essentials of organic chemistry: For students of pharmacy, medicinal chemistry and biological chemistry. Chichester, West Sussex, England: J. Wiley.

[2]McMurry, J., & Begley, T. P. (2016). The organic chemistry of biological pathways. Greenwood Village, CO: Roberts and Company.

[3]Ts'o, P. O., & Eisinger, J. (1974). Basic principles in nucleic acid chemistry. New York: Academic Press.

[4]Wang, C., Song, Z., Yu, H., Liu, K., & Ma, X. (2015). Adenine: an important drug scaffold for the design of antiviral agents. Acta Pharmaceutica Sinica. B, 5(5), 431–441. http://doi.org/10.1016/j.apsb.2015.07.002

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