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You are watching: What sugars are found in dna

Berg JM, Tymoczko JL, Stryer L. Biochemistry. Fifth edition. Brand-new York: W H Freeman; 2002.


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The nucleic acids DNA and also RNA are well suitable to function as the carrier of geneticinformation by virtue of your covalent structures. This macromolecules arelinear polymers built up from similar units connected end toend (Figure 5.1). Every monomer unit withinthe polymer is composed of 3 components: a sugar, a phosphate, and a base. Thesequence the bases unique characterizes a nucleic acid and also represents a form oflinear information.


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5.1.1. RNA and DNA different in the sugar Component and also One the the Bases

The sugar in deoxyribonucleic acid (DNA) isdeoxyribose. The deoxy prefix suggests that the 2′ carbonatom the the sugar lacks the oxygen atom the is linked to the 2′ carbon atom ofribose (the sugar in ribonucleic acid, orRNA), as displayed in Figure5.2. The street in main point acids are attached to one one more byphosphodiester bridges. Special, the 3′-hydroxyl (3′-OH) group of the sugarmoiety of one nucleotide is esterified to a phosphate group, i beg your pardon is, in turn,joined come the 5′-hydroxyl team of the nearby sugar. The chain that sugarslinked by phosphodiester bridges is described as the backboneof the nucleic mountain (Figure 5.3). Whereasthe backbone is consistent in DNA and RNA, the bases differ from one monomer come thenext. 2 of the bases are derivatives the purine—adenine (A)and guanine (G)—and two of pyrimidine—cytosine (C) and thymine(T, DNA only) or uracil (U, RNA only), as displayed in number 5.4.


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Figure 5.2

Ribose and also Deoxyribose. Atoms are numbered through primes to identify them from atoms 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 formed by 3′-to-5′phosphodiester linkages. A street unit is emphasize in red and aphosphate group in blue.


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Figure 5.4

Purines and Pyrimidines. Atom within bases are numbered there is no primes. Uracil instead ofthymine is offered in RNA.


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

Note the each phosphodiester bridge has a an unfavorable charge. This an unfavorable chargerepels nucleophilic types such together hydroxide ion; consequently, phosphodiesterlinkages are much less susceptible to hydrolytic strike than are various other esterssuch together carboxylic acid esters. This resistance is crucial for preserving theintegrity of info stored in nucleic acids. The absence of the 2′-hydroxylgroup in DNA further increases that is resistance to hydrolysis. The greaterstability that DNA most likely accounts for its use quite than RNA together the hereditarymaterial in all contemporary cells and also in plenty of viruses.


Structural Insights, main point Acids

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


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


Figure 5.6

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


The abbreviated symbol pApCpG or pACG represent a trinucleotide that DNA consistingof the structure blocks deoxyadenylate monophosphate, deoxycytidylatemonophosphate, and also deoxyguanylate monophosphate attached by a phosphodiesterbridge, wherein “p” denotes a phosphate group (Figure 5.7). The 5′ end will frequently have a phosphate attached come the5′-OH group. Keep in mind that, favor a polypeptide (see ar 3.2), a DNA chain has polarity. One finish ofthe chain has actually a cost-free 5′-OH group (or a 5′-OH team attached come a phosphate),whereas the other end has a 3′-OH group, neither of i beg your pardon is attached to anothernucleotide. By convention, the base sequence is written in the5′-to-3′ direction. Thus, thesymbol ACG shows that the unlinked 5′-OH team is ~ above deoxyadenylate, whereasthe unlinked 3′-OH team is on deoxyguanylate. Because of this polarity, ACG andGCA correspond to various compounds.


Figure 5.7

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


A striking properties of naturally arising DNA molecule is your length. ADNA molecule must make up many nucleotides to lug the genetic informationnecessary for even the easiest organisms. For example, the DNA that a virus suchas polyoma, which can cause cancer in details organisms, is as long as 5100nucleotides in length. We can quantify the details carrying volume ofnucleic mountain in the following way. Each position can be one of 4 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 the 4.6 million nucleotides, matching to 9.2 million bits, or1.15 megabytes, of info (Figure5.8).


Figure 5.8

Electron Micrograph of component of the E. Coligenome.


DNA molecule from higher organisms deserve to be much larger. The human genomecomprises about 3 billion nucleotides, divided amongst 24 distinct DNAmolecules (22 autosomes, x and y sex chromosomes) of different sizes. Among thelargest known DNA molecules is uncovered in the Indian muntjak, an Asiatic deer; itsgenome is nearly as huge as the person genome but is dispersed on just 3chromosomes (Figure 5.9). The largest ofthese chromosomes has actually chains of much more than 1 billion nucleotides. If together a DNAmolecule could be totally extended, it would stretch an ext than 1 foot in length.Some tree contain even larger DNA molecules.

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Figure 5.9

The Indian Muntjak and also Its Chromosomes. Cell from a female Indian muntjak (right) contain 3 pairs ofvery large chromosomes (stained orange). The cell shown is a hybridcontaining a pair of human being chromosomes (stained green) forcomparison. <(Left) (more...)


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