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2.11 Covalent Attachment on a Solid Support

DOI: 10.1055/sos-SD-241-00183

Franzini, R. M.Science of Synthesis: DNA-Encoded Libraries, (20241423.

General Introduction

The synthesis of DNA-encoded combinatorial libraries relies on reactions that are high yielding and devoid of side products. Reactions on DNA in solution need to be compatible with the functional groups on DNA, and also with the reaction medium, which typically contains water. These requirements restrict the chemical reactions and reagents that can be used on deprotected DNA. In some cases, it can therefore be advantageous to perform reactions directly on the solid support used for the synthesis of the DNA, because this strategy allows the use of anhydrous solvents, while the protecting groups of the exocyclic amines prevent side reactions. The approach is exemplified in Scheme 1; here, conjugation involves removal of the MMT protecting group with mild acid, followed by coupling of the carboxylic acid. Subsequent treatment with a concentrated aqueous solution of an amine removes the protecting groups and cleaves the DNA from the solid support.[‌1‌,‌2‌]

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