Abstract
We describe a simple method for the direct modification of nucleobases in cyclic purine dinucleotides, important signalling molecules in both prokaryotes and eukaryotes. The method tolerates all members of the cyclic dinucleotide family and could be used to modulate their function or introduce useful side-chains such as fluorophores and photo-crosslinking groups.
Highlights
Na Fei,a Daniel Haussinger,a Seraina Blumli,a Benoıt-Joseph Laventie,b Lorenzo D
We describe a simple method for the direct modification of nucleobases in cyclic purine dinucleotides, important signalling molecules in both prokaryotes and eukaryotes
The method tolerates all members of the cyclic dinucleotide family and could be used to modulate their function or introduce useful side-chains such as fluorophores and photo-crosslinking groups
Summary
Na Fei,a Daniel Haussinger,a Seraina Blumli,a Benoıt-Joseph Laventie,b Lorenzo D. While total chemical synthesis gives access to any variation, substantial expertise and labour are required.[7] Semi-syntheses from the natural CDNs are simpler, but until now these have focussed on changes in the phosphate linkage or 20 position of the ribose (see Fig. 2).[8] We report here that catalytic rhodium-based carbene transfer offers a one-step method to target the exocyclic amine of nucleobases in all types of natural 30-50-linked CDNs. Direct nucleobase modification has never been explored, but would provide an important complement to previous approaches.
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