Mateja Klika Škopić; Suzanne Willems; Bernd Wagner; Justin Schieven; Norbert Krause; Andreas Brunschweiger
Org. Biomol. Chem., 2017, 15, 8648-8654
https://doi.org/10.1039/c7ob02347b

Abstract

We demonstrate a Au(I)-mediated three-component reaction to DNA-tagged highly substituted 6-oxa-1,2-diazaspiro[4.4]nonanes from either DNA-coupled aldehydes, hydrazides, or alkynols. The choice of the starting material coupled to the DNA tag was critial for the purity of the product as the DNA-aldehyde conjugate yielded the purest products, whereas the alkynol- and hydrazide conjugates returned complex product mixtures. The reaction was compatible with thymine-, cytosine-, and, surprisingly, with adenine-DNA, while guanine-containing DNA strands were degraded under the reaction conditions.