New thermolytic carbamoyl groups for the protection of nucleobases.
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.
Ohkubo
Akihiro
A
Department of Life Science, Tokyo Institute of Technology, 4259, Nagatsuta, Midoriku, Yokohama 226-8501, Japan.
Kasuya
Rintaro
R
Miyata
Kenichi
K
Tsunoda
Hirosuke
H
Seio
Kohji
K
Sekine
Mitsuo
M
D002219:Carbamates / Q000737:chemistry; D015342:DNA Probes / Q000138:chemical synthesis*; D003839:Deoxyadenosines / Q000737:chemistry; D003841:Deoxycytidine / Q000737:chemistry; D006358:Hot Temperature; D009694:Nucleic Acid Precursors / Q000138:chemical synthesis*
D002219:Carbamates; D015342:DNA Probes; D003839:Deoxyadenosines; D009694:Nucleic Acid Precursors; D003841:Deoxycytidine; C070766:carbamic acid