CHEM564 Lecture Notes - Lecture 15: Sodium Periodate, Propargyl, Angewandte Chemie

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The structure of oligonucleotides consists of individual nucleotides linked by a phosphodiester. Dna/rna synthesis is now done routinely using established protocols, and can often be obtained from commercial sources. The versatility of oligonucleotide synthesis is a central technology for molecular biology, as it is used to generate specific primers and other reagents necessary for these methods. Several strategies have been developed for the synthesis of oligonucleotides. The central problem to be solved in oligonucleotide synthesis is the efficient generation of the phosphodiester. A brief summary in approximate chronological order is given below. Coupling using a phosphate was one of the earliest strategies applied. In the scheme below, where x is a good leaving group. An example would be the use of tscl to form the tosylated phosphate ester, which is then reactive with the 3"-oh of the other residue. Coupling reagents, such as carbodiimides may also be used to accelerate this type of coupling.