title: New thermolytic carbamoyl groups for the protection of nucleobases.
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.
authors.affiliation: Department of Life Science, Tokyo Institute of Technology, 4259, Nagatsuta, Midoriku, Yokohama 226-8501, Japan.
authors.forename: Akihiro
authors.initials: A
authors.lastname: Ohkubo
authors.forename: Rintaro
authors.initials: R
authors.lastname: Kasuya
authors.forename: Kenichi
authors.initials: K
authors.lastname: Miyata
authors.forename: Hirosuke
authors.initials: H
authors.lastname: Tsunoda
authors.forename: Kohji
authors.initials: K
authors.lastname: Seio
authors.forename: Mitsuo
authors.initials: M
authors.lastname: Sekine
mesh_terms: 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*
chemical_list: D002219:Carbamates; D015342:DNA Probes; D003839:Deoxyadenosines; D009694:Nucleic Acid Precursors; D003841:Deoxycytidine; C070766:carbamic acid