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You are watching: What sugar distinguishes rna from dna

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


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The nucleic acids DNA and also RNA are well suitable to role as the carriers of geneticinformation by virtue of their covalent structures. This macromolecules arelinear polymers accumulated from similar units connected end toend (Figure 5.1). Each monomer unit withinthe polymer is composed of 3 components: a sugar, a phosphate, and a base. Thesequence the bases uniquely characterizes a main point acid and also represents a kind oflinear information.


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

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


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Figure 5.2

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


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Figure 5.3

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


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Figure 5.4

Purines and Pyrimidines. Atom within bases space numbered without primes. Uracil rather ofthymine is supplied in RNA.


RNA, like DNA, is a lengthy unbranched polymer consist of of nucleotides join by3′→5′ phosphodiester bond (see Figure5.3). The covalent framework of RNA differs from the of DNA in tworespects. As proclaimed earlier and as suggested by that name, the sugar units in RNAare riboses rather than deoxyriboses. Ribose has a 2′-hydroxyl group notpresent in deoxyribose. Together a consequence, in enhancement to the standard 3′→5′linkage, a 2′→5′ affiliation is possible for RNA. This later linkage is essential inthe remove of introns and also the joining of exons for the development of tires RNA(Section 28.3.4). The otherdifference, as currently mentioned, is that one of the four major bases in RNA isuracil (U) rather of thymine (T).

Note that each phosphodiester bridge has actually a an adverse charge. This negative chargerepels nucleophilic species such as hydroxide ion; consequently, phosphodiesterlinkages space much much less susceptible to hydrolytic attack than are other esterssuch together carboxylic acid esters. This resistance is an important for maintaining theintegrity of info stored in main point acids. The lack of the 2′-hydroxylgroup in DNA more increases its resistance come hydrolysis. The greaterstability that DNA more than likely accounts for its use rather than RNA as the hereditarymaterial in all contemporary cells and in countless viruses.


Structural Insights, main point Acids

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


A unit consisting of a basic bonded come a street is described as anucleoside. The 4 nucleosideunits in RNA are called adenosine, guanosine, cytidine, anduridine, vice versa, those in DNA are calleddeoxyadenosine, deoxyguanosine, deoxycytidine, andthymidine. In every case, N-9 that a purine or N-1 that apyrimidine is attached come C-1′ of the sugar (Figure 5.5). The base lies over the plane of sugar once thestructure is composed in the typical orientation; the is, the configuration ofthe N-glycosidic affiliation is β. Anucleotide is a nucleosidejoined to one or more phosphate groups by one ester linkage. The most typical siteof esterification in naturally developing nucleotides is the hydroxyl groupattached to C-5′ that the sugar. A compound created by the attachment of aphosphate team to the C-5′ of a nucleoside sugar is called a nucleoside5′-phosphate or a5′-nucleotide. Because that example, ATP isadenosine 5′-triphosphate. Anothernucleotide is deoxyguanosine 3′-monophosphate (3′-dGMP; number 5.6). This nucleotide differs from ATP in that itcontains guanine quite than adenine, has deoxyribose fairly than ribose(indicated by the prefix “d”), contains one rather than 3 phosphates, andhas the phosphate esterified come the hydroxyl group in the 3′ rather than the 5′position. Nucleotides room the monomers the are attached to form RNA and also DNA. Thefour nucleotide systems in DNA are called deoxyadenylate, deoxyguanylate,deoxycytidylate, and also deoxythymidylate, andthymidylate. Keep in mind that thymidylate consists of deoxyribose; byconvention, the prefix deoxy is not included because thymine-containing nucleotidesare just rarely discovered in RNA.


Figure 5.6

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


The abbreviated symbol pApCpG or pACG denote a trinucleotide of DNA consistingof the structure blocks deoxyadenylate monophosphate, deoxycytidylatemonophosphate, and deoxyguanylate monophosphate connected by a phosphodiesterbridge, where “p” denotes a phosphate team (Figure 5.7). The 5′ end will regularly have a phosphate attached come the5′-OH group. Note that, like a polypeptide (see ar 3.2), a DNA chain has actually polarity. One finish ofthe chain has actually a complimentary 5′-OH group (or a 5′-OH team attached to a phosphate),whereas the other end has a 3′-OH group, neither of i beg your pardon is linked to anothernucleotide. Through convention, the basic sequence is written in the5′-to-3′ direction. Thus, thesymbol ACG shows that the unlinked 5′-OH team is top top deoxyadenylate, whereasthe unlinked 3′-OH group is on deoxyguanylate. Because of this polarity, ACG andGCA exchange mail to various compounds.


Figure 5.7

Structure that a DNA Chain. The chain has a 5′ end, i beg your pardon is commonly attached to a phosphate, anda 3′ end, i m sorry is usually a complimentary hydroxyl group.


A striking characteristic of naturally arising DNA molecules is their length. ADNA molecule must consist of many nucleotides to bring the hereditary informationnecessary for even the easiest organisms. For example, the DNA that a virus suchas polyoma, which can cause cancer in specific organisms, is as lengthy as 5100nucleotides in length. We have the right to quantify the info carrying volume ofnucleic acids in the following way. Every position can be one of 4 bases,corresponding to 2 bits of info (22 = 4). Thus, a chain of5100 nucleotides coincides to 2 × 5100 = 10,200 bits, or 1275 bytes (1 byte =8 bits). The E. Coli genome is a solitary DNA molecule consistingof 2 chains that 4.6 million nucleotides, equivalent to 9.2 million bits, or1.15 megabytes, of info (Figure5.8).


Figure 5.8

Electron Micrograph of component of the E. Coligenome.


DNA molecules from higher organisms have the right to be much larger. The person genomecomprises roughly 3 exchange rate nucleotides, divided among 24 unique DNAmolecules (22 autosomes, x and also y sex chromosomes) of various sizes. One of thelargest recognized DNA molecule is found in the Indian muntjak, one Asiatic deer; itsgenome is almost as big as the human being genome but is dispersed on just 3chromosomes (Figure 5.9). The biggest ofthese chromosomes has chains of an ext than 1 billion nucleotides. If such a DNAmolecule could be completely extended, it would certainly stretch more than 1 foot in length.Some plants contain even larger DNA molecules.

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Figure 5.9

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


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