Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction

• Vicky Gheerardijn,
• Jos Van den Begin and
• Annemieke Madder

Beilstein J. Org. Chem. 2014, 10, 2566–2572, doi:10.3762/bjoc.10.268

• -intermediates in DNA- and RNAzymes via an efficient and straightforward domino carboxamidation reaction. Keywords: amino acids; bioorganic chemistry; carboxamidation reaction; chemically modified; DNA nucleosides; nucleic acids; Introduction For decades DNA has been known as the carrier of the genetic

• lysine derivatives onto nucleosides via a straightforward and easy domino carboxamidation reaction. Previously the groups of Gait and Eaton [41][42][43] have used this reaction to couple histamine or simple amine derivatives to both 5-iodo-2’-deoxyuridine and purine nucleosides. Although a large number

• . For the introduction of histidine onto the nucleoside as shown in Scheme 1, we chose to protect the free 3’ and 5’-hydroxy groups with tert-butyldimethylsilyl (TBDMS) groups 1 to avoid side reactions during the next step, the carboxamidation reaction [48]. While protected histidine is commercially