Modifying Biomacromolecules

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Biomacromolecules are oligomeric molecules that are composed of smaller building blocks in nature. The three major classes of biomacromolecules are proteins, nucleic acids, and polysaccha-rides, built up of amino acids, nucleotides, and carbohydrates, respectively.

The modification of nucleic acids is a very promising and fruitful area of research, where peptide nucleic acid (PNA) and locked nucleic acid (LNA) are prominent examples of modified nucleic acids (Figure 4.5). In PNA, the deoxyribose of the DNA backbone is replaced with ^-(2-aminoethyl)-glycine units. This has several advantages, for example, the backbone is linked by peptide bonds,

dna pna lna

FIGURE 4.5 Examples of two very successful modified structures of DNA/RNA: PNA, where the deoxyribose of the DNA backbone is replaced with A-(2-aminoethyl)-glycine units, and LNA, where the ribose moiety is modified with an extra bridge connecting the 2' and 4' carbons.

dna pna lna

FIGURE 4.5 Examples of two very successful modified structures of DNA/RNA: PNA, where the deoxyribose of the DNA backbone is replaced with A-(2-aminoethyl)-glycine units, and LNA, where the ribose moiety is modified with an extra bridge connecting the 2' and 4' carbons.

thus synthesis is easier and also the stability of PNA is increased compared to DNA. Another prominent example of DNA, or rather RNA, modification is LNA, where the ribose moiety of an LNA nucleotide is modified with an extra bridge connecting the 2' and 4' carbons (Figure 4.5). The bridge locks the ribose in the 3'-endo structural conformation, which is supposed to be an important bioactive conformation. This locked conformation of LNA enhances base stacking and backbone preorganization, as well as increases the stability of the nucleic acids. Both PNA and LNA are being pursued commercially as potential drug candidates, as well as diagnostic tools. Polysaccharides, such as starch and glycogen, are highly important biomacromolecules, and the term "glycomics" has been introduced analogous to genomics and proteomics, to describe the comprehensive study of sugars in organisms, and glycomics is a subset of studies of sugars in biology in general, termed glycobiology. Carbohydrates also play vital roles as posttranslational modifications (PTMs) of gly-coproteins and in the remainder of this chapter focus will be on proteins and methods for modifying proteins.

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