Issue 4, 2009

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.

Graphical abstract: New thermolytic carbamoyl groups for the protection of nucleobases

Supplementary files

Article information

Article type
Paper
Submitted
01 Oct 2008
Accepted
19 Nov 2008
First published
07 Jan 2009

Org. Biomol. Chem., 2009,7, 687-694

New thermolytic carbamoyl groups for the protection of nucleobases

A. Ohkubo, R. Kasuya, K. Miyata, H. Tsunoda, K. Seio and M. Sekine, Org. Biomol. Chem., 2009, 7, 687 DOI: 10.1039/B816831H

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