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2.10 Reversible Immobilization of DNA for Chemical Modification

DOI: 10.1055/sos-SD-241-00207

Franzini, R. M.Science of Synthesis: DNA Encoded Librariesearly view.

General Introduction

The synthesis of complex molecules on solid supports has been widely carried out in combinatorial chemistry.[‌1‌] The preparation of DNA-encoded chemical libraries, however, mostly involves reactions in solution. Solid-phase protocols could offer advantages because they make it possible to expose a modified DNA to several cycles of freshly prepared reagents, to elute excess reagents, and to use anhydrous conditions. Synthesis on a solid support (see Section 2.11) could be preferrable for DNA-encoded library preparation, but is mostly restricted to reactions at cycle 1. Alternatively, it is possible to reversibly immobilize DNA on an anion-exchange resin or other support, and proceed as if the DNA was covalently attached to this support (Scheme 1). This “pseudo-solid-phase” approach was first described by Harbury et al. using DEAE Sepharose as the support (Section 2.10.1.1).[‌2‌] However, it should be noted that the utility of DEAE Sepharose is limited to certain water-compatible reactions such as amide-bond formation and nucleophilic substitution.[‌3‌] The use of strong anion-exchange resins (e.g., PEG+, a cationic, amphiphilic PEG-based polymer; Section 2.10.1.2) allows access to a much broader scope of reactions, including those requiring anhydrous conditions.[‌4‌,‌5‌]

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References


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