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You are watching: What sugar is found in dna

Berg JM, Tymoczko JL, Stryer L. Biochemistry. 5th edition. New York: W H Freeman; 2002.


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The main point acids DNA and RNA space well suited to role as the carriers of geneticinformation by virtue of your covalent structures. This macromolecules arelinear polymers gathered from similar units associated end toend (Figure 5.1). Every monomer unit withinthe polymer consists of three components: a sugar, a phosphate, and also a base. Thesequence of bases unique characterizes a nucleic acid and represents a type oflinear information.


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5.1.1. RNA and DNA differ in the street Component and also One of the Bases

The sugar in deoxyribonucleic mountain (DNA) isdeoxyribose. The deoxy prefix suggests that the 2′ carbonatom the the sugar lacks the oxygen atom the is connected to the 2′ carbon atom ofribose (the sugar in ribonucleic acid, orRNA), as shown in Figure5.2. The sugars in nucleic acids are attached to one an additional byphosphodiester bridges. Specifically, the 3′-hydroxyl (3′-OH) team of the sugarmoiety of one nucleotide is esterified to a phosphate group, i m sorry is, in turn,joined to the 5′-hydroxyl group of the nearby sugar. The chain that sugarslinked through phosphodiester bridges is described as the backboneof the nucleic mountain (Figure 5.3). Whereasthe backbone is constant in DNA and also RNA, the bases vary from one monomer to thenext. Two of the bases room derivatives of purine—adenine (A)and guanine (G)—and 2 of pyrimidine—cytosine (C) and thymine(T, DNA only) or uracil (U, RNA only), as presented in number 5.4.


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Figure 5.2

Ribose and also Deoxyribose. Atoms are numbered through primes to distinguish them from atom inbases (see figure 5.4).


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Figure 5.3

Backbones the DNA and also RNA. The backbones that these nucleic acids are developed by 3′-to-5′phosphodiester linkages. A street unit is emphasize in red and aphosphate team in blue.


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Figure 5.4

Purines and Pyrimidines. Atoms within bases space numbered there is no primes. Uracil instead ofthymine is provided in RNA.


RNA, prefer DNA, is a long unbranched polymer consisting of nucleotides join by3′→5′ phosphodiester bond (see Figure5.3). The covalent structure of RNA differs from the of DNA in tworespects. As declared earlier and also as suggested by that is name, the sugar units in RNAare riboses rather than deoxyriboses. Ribose contains a 2′-hydroxyl team notpresent in deoxyribose. As a consequence, in enhancement to the traditional 3′→5′linkage, a 2′→5′ link is feasible for RNA. This later linkage is important inthe remove of introns and also the authorized of exons for the development of mature RNA(Section 28.3.4). The otherdifference, as already mentioned, is that among the four major bases in RNA isuracil (U) instead of thymine (T).

Note the each phosphodiester bridge has a an adverse charge. This an unfavorable chargerepels nucleophilic varieties such together hydroxide ion; consequently, phosphodiesterlinkages space much much less susceptible come hydrolytic attack than are various other esterssuch as carboxylic acid esters. This resistance is crucial for preserving theintegrity of information stored in main point acids. The lack of the 2′-hydroxylgroup in DNA additional increases its resistance come hydrolysis. The greaterstability the DNA probably accounts for its use fairly than RNA as the hereditarymaterial in all modern-day cells and also in plenty of viruses.


Structural Insights, main point Acids

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offers a three-dimensional view on nucleotide structure, basepairing, and also other facets of DNA and RNA structure.


A unit consisting of a basic bonded come a street is described as anucleoside. The four nucleosideunits in RNA are referred to as adenosine, guanosine, cytidine, anduridine, conversely, those in DNA room calleddeoxyadenosine, deoxyguanosine, deoxycytidine, andthymidine. In each case, N-9 the a purine or N-1 of apyrimidine is attached come C-1′ that the street (Figure 5.5). The basic lies over the aircraft of sugar as soon as thestructure is created in the standard orientation; the is, the construction ofthe N-glycosidic link is β. Anucleotide is a nucleosidejoined to one or much more phosphate groups by an ester linkage. The most typical siteof esterification in naturally occurring nucleotides is the hydroxyl groupattached to C-5′ of the sugar. A compound developed by the attachment of aphosphate group to the C-5′ of a nucleoside sugar is called a nucleoside5′-phosphate or a5′-nucleotide. For example, ATP isadenosine 5′-triphosphate. Anothernucleotide is deoxyguanosine 3′-monophosphate (3′-dGMP; number 5.6). This nucleotide different from ATP in that itcontains guanine rather than adenine, contains deoxyribose rather than ribose(indicated through the prefix “d”), consists of one quite than three phosphates, andhas the phosphate esterified to the hydroxyl group in the 3′ rather than the 5′position. Nucleotides are the monomers that are linked to type RNA and also DNA. Thefour nucleotide units in DNA are referred to as deoxyadenylate, deoxyguanylate,deoxycytidylate, and deoxythymidylate, andthymidylate. Note that thymidylate consists of deoxyribose; byconvention, the prefix deoxy is not added because thymine-containing nucleotidesare just rarely found in RNA.


Figure 5.6

Nucleotides adenosene 5′ -triphosphate (5′-ATP) anddeoxyguanosine 3′-monophosphate (3′-dGMP).


The abbreviated symbol pApCpG or pACG signify a trinucleotide the DNA consistingof the building blocks deoxyadenylate monophosphate, deoxycytidylatemonophosphate, and deoxyguanylate monophosphate connected by a phosphodiesterbridge, wherein “p” denotes a phosphate group (Figure 5.7). The 5′ end will often have a phosphate attached come the5′-OH group. Keep in mind that, like a polypeptide (see ar 3.2), a DNA chain has actually polarity. One end ofthe chain has actually a cost-free 5′-OH group (or a 5′-OH team attached to a phosphate),whereas the other end has a 3′-OH group, no of which is connected to anothernucleotide. Through convention, the base sequence is composed in the5′-to-3′ direction. Thus, thesymbol ACG shows that the unlinked 5′-OH team is ~ above deoxyadenylate, whereasthe unlinked 3′-OH team is ~ above deoxyguanylate. Because of this polarity, ACG andGCA correspond to different compounds.


Figure 5.7

Structure the a DNA Chain. The chain has a 5′ end, i m sorry is usually attached to a phosphate, anda 3′ end, i m sorry is typically a free hydroxyl group.


A striking characteristic of naturally developing DNA molecules is their length. ADNA molecule must make up many nucleotides to lug the hereditary informationnecessary for also the most basic organisms. For example, the DNA that a virus suchas polyoma, i m sorry can reason cancer in certain organisms, is as long as 5100nucleotides in length. We can quantify the information carrying capacity ofnucleic mountain in the complying with way. Each position deserve to be one of four bases,corresponding to 2 bits of info (22 = 4). Thus, a chain of5100 nucleotides synchronizes to 2 × 5100 = 10,200 bits, or 1275 bytes (1 byte =8 bits). The E. Coli genome is a solitary DNA molecule consistingof two chains that 4.6 million nucleotides, corresponding to 9.2 million bits, or1.15 megabytes, of details (Figure5.8).


Figure 5.8

Electron Micrograph of part of the E. Coligenome.


DNA molecules from higher organisms have the right to be lot larger. The human being genomecomprises roughly 3 exchange rate nucleotides, divided among 24 distinctive DNAmolecules (22 autosomes, x and also y sex chromosomes) of different sizes. Among thelargest well-known DNA molecules is discovered in the Indian muntjak, one Asiatic deer; itsgenome is virtually as big as the human being genome however is distributed on only 3chromosomes (Figure 5.9). The largest ofthese chromosomes has chains of much more than 1 billion nucleotides. If together a DNAmolecule could be completely extended, it would certainly stretch more than 1 foot in length.Some tree contain also larger DNA molecules.

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Figure 5.9

The Indian Muntjak and also Its Chromosomes. Cell from a woman Indian muntjak (right) contain 3 pairs ofvery huge chromosomes (stained orange). The cell displayed is a hybridcontaining a pair of person chromosomes (stained green) forcomparison. <(Left) (more...)


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