New thermolytic carbamoyl groups for the protection of nucleobases
Akihiro Ohkubo1, Rintaro Kasuya, Kenichi Miyata
1Department of Life Science, Tokyo Institute of Technology, 4259, Nagatsuta, Midoriku, Yokohama 226-8501, Japan.
Abstract:
It was found that N-arylcarbamoyl and N-(phenylsulfonyl)carbamoyl (psc) groups could be effectively introduced onto the amino groups of deoxycytidine and deoxyadenosine derivatives and could be removed thermolytically. We succeeded in synthesizing DNA probes incorporating these thermo-removable protecting groups and developed a new system for molecular switching by changing the protection- and deprotection-modes using simple heating and re-carbamoylation with isocyanates. This reversible process enabled us to control the hybridization ability of the DNA probes.
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