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New thermolytic carbamoyl groups for the protection of nucleobases.

Authors
  • Ohkubo, Akihiro
  • Kasuya, Rintaro
  • Miyata, Kenichi
  • Tsunoda, Hirosuke
  • Seio, Kohji
  • Sekine, Mitsuo
Type
Published Article
Journal
Organic & Biomolecular Chemistry
Publisher
The Royal Society of Chemistry
Publication Date
Feb 21, 2009
Volume
7
Issue
4
Pages
687–694
Identifiers
DOI: 10.1039/b816831h
PMID: 19194584
Source
Medline
License
Unknown

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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