{"id":2123,"date":"2018-03-21T20:34:46","date_gmt":"2018-03-21T20:34:46","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-orgbiochemistry\/?post_type=chapter&p=2123"},"modified":"2018-05-09T18:48:39","modified_gmt":"2018-05-09T18:48:39","slug":"19-1-nucleotides","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-monroecc-orgbiochemistry\/chapter\/19-1-nucleotides\/","title":{"raw":"19.1 Nucleotides","rendered":"19.1 Nucleotides"},"content":{"raw":"
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Learning Objective<\/h3>\r\n
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  1. Identify the different molecules that combine to form nucleotides.<\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n

    The repeating, or monomer, units that are linked together to form nucleic acids are known as. The deoxyribonucleic acid (DNA) of a typical mammalian cell contains about 3 \u00d7 109<\/sup> nucleotides. Nucleotides can be further broken down to phosphoric acid (H3<\/sub>PO4<\/sub>), a pentose sugar (a sugar with five carbon atoms), and a nitrogenous base (a base containing nitrogen atoms).<\/p>\r\n nucleic\u00a0acids\u00a0\u2192down\u00a0intocan\u00a0be\u00a0broken\u00a0nucleotides\u2192down\u00a0intocan\u00a0be\u00a0broken\u00a0H3<\/sub>PO4<\/sub>\u00a0+\u00a0nitrogen\u00a0base\u00a0+\u00a0pentose\u00a0sugar <\/span>\r\n

    If the pentose sugar is ribose, the nucleotide is more specifically referred to as a ribonucleotide<\/em>, and the resulting nucleic acid is ribonucleic acid (RNA). If the sugar is 2-deoxyribose, the nucleotide is a deoxyribonucleotide<\/em>, and the nucleic acid is DNA.<\/p>\r\n\r\n

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    The nitrogenous bases found in nucleotides are classified as pyrimidines<\/span><\/span>\u00a0or purines<\/span><\/span>. Pyrimidines are heterocyclic amines with two nitrogen atoms in a six-member ring and include uracil, thymine, and cytosine. (For more information about heterocyclic amines, see Chapter 15 \"Organic Acids and Bases and Some of Their Derivatives\"<\/a>, Section 15.13 \"Amines as Bases\"<\/a>.) Purines are heterocyclic amines consisting of a pyrimidine ring fused to a five-member ring with two nitrogen atoms. Adenine and guanine are the major purines found in nucleic acids (Figure 19.2 \"The Nitrogenous Bases Found in DNA and RNA\"<\/a>).<\/p>\r\n\r\n

    \r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"1500\"]\"image\" Figure 19.2 The Nitrogenous Bases Found in DNA and RNA <\/em>[\/caption]\r\n\r\n<\/div>\r\n

    The formation of a bond between C1\u2032 of the pentose sugar and N1 of the pyrimidine base or N9 of the purine base joins the pentose sugar to the nitrogenous base. In the formation of this bond, a molecule of water is removed. Table 19.1 \"Composition of Nucleotides in DNA and RNA\"<\/a> summarizes the similarities and differences in the composition of nucleotides in DNA and RNA.<\/p>\r\n\r\n

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    Note<\/h3>\r\n

    The numbering convention is that primed numbers designate the atoms of the pentose ring, and unprimed numbers designate the atoms of the purine or pyrimidine ring.<\/p>\r\n\r\n<\/div>\r\n<\/div>\r\n

    Table 19.1 Composition of Nucleotides in DNA and RNA<\/span><\/h3>\r\n<\/div>\r\n
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    Composition<\/th>\r\nDNA<\/th>\r\nRNA<\/th>\r\n<\/tr>\r\n<\/thead>\r\n
    purine bases<\/td>\r\nadenine and guanine<\/td>\r\nadenine and guanine<\/td>\r\n<\/tr>\r\n
    pyrimidine bases<\/td>\r\ncytosine and thymine<\/td>\r\ncytosine and uracil<\/td>\r\n<\/tr>\r\n
    pentose sugar<\/td>\r\n2-deoxyribose<\/td>\r\nribose<\/td>\r\n<\/tr>\r\n
    inorganic acid<\/td>\r\nphosphoric acid (H3<\/sub>PO4<\/sub>)<\/td>\r\nH3<\/sub>PO4<\/sub><\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<\/div>\r\n

    The names and structures of the major ribonucleotides and one of the deoxyribonucleotides are given in Figure 19.3 \"The Pyrimidine and Purine Nucleotides\"<\/a>.<\/p>\r\n\r\n

    \r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"1500\"]\"image\" Figure 19.3 The Pyrimidine and Purine Nucleotides <\/em>[\/caption]\r\n\r\n<\/div>\r\n

    Apart from being the monomer units of DNA and RNA, the nucleotides and some of their derivatives have other functions as well. Adenosine diphosphate (ADP) and adenosine triphosphate (ATP), shown in Figure 19.4 \"Structures of Two Important Adenine-Containing Nucleotides\"<\/a>, have a role in cell metabolism that we will discuss in Chapter 20 \"Energy Metabolism\"<\/a>. Moreover, a number of coenzymes, including flavin adenine dinucleotide (FAD), nicotinamide adenine dinucleotide (NAD+<\/sup>), and coenzyme A, contain adenine nucleotides as structural components. (For more information on coenzymes, see Chapter 18 \"Amino Acids, Proteins, and Enzymes\"<\/a>, Section 18.9 \"Enzyme Cofactors and Vitamins\"<\/a>.)<\/p>\r\n\r\n

    \r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"1500\"]\"image\" Figure 19.4 Structures of Two Important Adenine-Containing Nucleotides<\/em>[\/caption]\r\n\r\n<\/div>\r\n
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    Concept Review Exercises<\/h3>\r\n
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    1. \r\n
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      Identify the three molecules needed to form the nucleotides in each nucleic acid.<\/p>\r\n\r\n

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      1. DNA<\/li>\r\n \t
      2. RNA<\/li>\r\n<\/ol>\r\n<\/div><\/li>\r\n \t
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        Classify each compound as a pentose sugar, a purine, or a pyrimidine.<\/p>\r\n\r\n

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        1. adenine<\/li>\r\n \t
        2. guanine<\/li>\r\n \t
        3. deoxyribose<\/li>\r\n \t
        4. thymine<\/li>\r\n \t
        5. ribose<\/li>\r\n \t
        6. cytosine<\/li>\r\n<\/ol>\r\n<\/div><\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n
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          Answers<\/h3>\r\n[reveal-answer q=\"730316\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"730316\"]\r\n\r\n1. 1. nitrogenous base (adenine, guanine, cytosine, and thymine), 2-deoxyribose, and H3<\/sub>PO4<\/sub>\r\n\r\n2. nitrogenous base (adenine, guanine, cytosine, and uracil), ribose, and H3<\/sub>PO4<\/sub>\r\n\r\n2. 1. purine\r\n\r\n2. purine\r\n\r\n3. pentose sugar\r\n\r\n4. pyrimidine\r\n\r\n5. pentose sugar\r\n\r\n6. pyrimidine[\/hidden-answer]\u00a0<\/span>\r\n\r\n<\/div>\r\n<\/div>\r\n
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          Key Takeaways<\/h3>\r\n<\/div>\r\n
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