Lecture37outline

Lecture37outline - I Review DNA synthesis can be achieved...

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I. Review • DNA synthesis can be achieved through automated solid phase synthesis that employs protected subunits • Bases can be appended to deoxyribose through S N 2 reactions between protected bases and ditoluoyl deoxyribosyl chloride (a compound that can be purified as a single stereoisomer through crystallization) • The toluoyl groups are esters that can be cleaved by hydroxide • The primary 5'-hydroxyl group can be protected selectively in the presence of the secondary 3'-hydroxyl group through an S N 1 reaction with dimethoxytrityl (di- para - methoxyphenyl benzyl chloride, DMTCl) • The 3'-hydroxyl group can react with cyanoethyl diisopropylamino chlorophosphite in preparation for phosphodiester linkage synthesis • The functionalized, protected subunit reacts with a polymer-bound DNA chain with an unprotected 5'-hydroxyl group through displacement of the diisopropylamino group • The DMT group can readily be cleaved by adding Cl 3 CCO 2 H and the process can be continued
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Lecture37outline - I Review DNA synthesis can be achieved...

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