Nucleic acids sugar groups

Nucleic Acids. Phosphoms is an essential component of nucleic acids, polymers consisting of chains of nucleosides, a sugar plus a nitrogenous base, and joined by phosphate groups (43,44). In ribonucleic acid (RNA), the sugar is D-ribose in deoxyribonucleic acids (DNA), the sugar is 2-deoxy-D-ribose. 

Just as proteins are biopolymers made of amino acids, nucleic acids are biopolv-mers made of nucleotides joined together to form a long chain. Each nucleotide is composed of a nucleoside bonded to a phosphate group, and each nucleoside is composed of an aldopentose sugar linked through its anomeric carbon to the nitrogen atom of a heterocyclic purine or pyrimidine base. 

A nucleic acid polymer contains nucleotide chains in which the phosphate group of one nucleotide links to the sugar ring of a second. The resulting backbone is an alternating sequence of sugars and phosphates, as shown in... 

The nucleic acids, deoxyribonucleic acid (DNA) and ribonucleic acid (RNA), which carry embedded in their complex molecules the genetic information that characterizes every organism, are found in virtually all living cells. Their molecules are very large and complex biopolymers made up basically of monomeric units known as nucleotides. Thus DNA and RNA are said to be polynucleotides. The nucleotides are made up of three bonded (linked) components a sugar, a nitrogenous base, and one or more phosphate groups ... 

Oligonucleotides with modified sugar components are another alternative to PNAs work in this direction was begun by Albert Eschenmoser, a famous synthetic chemist who was interested in the question as to why nature chose certain biomolecules for the processes of life and not others (Eschenmoser, 1991). This group carried out studies on the sugar components of the nucleic acids, in order to find out why D-ribose was used rather than another sugar. 

Figure 1.42 The three pyrimidine bases common to nucleic acid construction. Cytosine and thymine are found in DNA, while in RNA, uracil residues replace thymine. The associated sugar groups are bound in N-glycosidic linkages to the N-l nitrogen.

However, there are particular sites that can be modified on the bases, sugars, or phosphate groups of nucleic acids to produce derivatives able to couple with a second molecule. The chemistry is almost entirely unique to DNA and RNA work, but once mastered, the process of conjugation can be done with the same ease as with protein molecules. 

The formation of an aldehyde group on a macromolecule can produce an extremely useful derivative for subsequent modification or conjugation reactions. In their native state, proteins, peptides, nucleic acids, and oligonucleotides contain no naturally occurring aldehyde residues. There are no aldehydes on amino acid side chains, none introduced by post-translational modifications, and no formyl groups on any of the bases or sugars of DNA and RNA. To create reactive aldehydes at specific locations within these molecules opens the possibility of directing modification reactions toward discrete sites within the macromolecule. 

To modify the unique chemical groups on nucleic acids, novel methods have been developed that allow derivatization through discrete sites on the available bases, sugars, or phosphate groups (see Chapter 1, Section 3 for a discussion of RNA and DNA structure). These chemical methods can be used to add a functional group or a label to an individual nucleotide or to one or more sites in oligonucleotide probes or full-sized DNA or RNA polymers. 

Weith, H.L., Wiebers, J.L., and Gilham, P.T. (1970) Synthesis of cellulose derivatives containing the dihy-droxyboryl group and a study of their capacity to form specific complexes with sugars and nucleic acid components. Biochemistry 9, 4396-4401. 

Tipson devoted most of his years in Levene s laboratory accomplishing seminal work on the components of nucleic acids. To determine the ring forms of the ribose component of the ribonucleosides he applied Haworth s methylation technique and established the furanoid structure for the sugar in adenosine, guanosine, uridine, and thymidine. He showed that formation of a monotrityl ether is not a reliable proof for the presence of a primary alcohol group in a nucleoside, whereas a tosyl ester that is readily displaced by iodide affords clear evidence that the ester is at the 5-position of the pentofuranose. Acetonation of ribonucleosides was shown to give the 2, 3 -C -isopropyl-idene derivatives, which were to become extensively used in nucleoside and nucleotide chemistry, and were utilized by Tipson in the first chemical preparation of a ribonucleotide, inosinic acid. 

In RNA, the base T found in DNA is replaced by uracil, which is similar in structure to T, but lacks the methyl group. The nucleotides in nucleic acids are linked by phosphodiester bonds between the 3 -hydroxyl of one nucleoside and the 5 -hydroxyl of the sugar of its neighbour in the sequence, as was first shown by Alexander Todd3 in 1952 (Figure 4.13). 

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