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  • Title: Synthesis, characterization, and application of substituted pyrazolopyrimidine nucleosides.
    Author: Dempcy RO, Podyminogin MA, Reed MW.
    Journal: Curr Protoc Nucleic Acid Chem; 2003 Feb; Chapter 1():1.8.1-1.8.15. PubMed ID: 18428901.
    Abstract:
    This unit describes, in detail, the preparation of 3-aminopropyl-substituted pyrazolo[3,4-d]pyrimidine analogs of the purines deoxyadenosine (dA) and deoxyguanosine (dG). Phosphoramidite reagents of these so-called aminopropyl-PPA and -PPG nucleosides (AP-PPA and AP-PPG, respectively) allow introduction of amino linkers into internal positions of synthetic DNA strands. Synthesis of suitably protected AP-PPA and AP-PPG phosphoramidites are described. The stepwise alkynylation, hydrogenation, selective protection, and phosphoramidite synthesis is similar for both the PPA and PPG analogs. To demonstrate the application of these reagents, a protocol is given in which a simple DNA strand is synthesized and conjugated to a lipophilic activated ester (dabcyl-SE) to form a stable amide linkage. Utility of this chemistry for preparing internally modified DNA conjugates is discussed.
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