New thermolytic carbamoyl groups for the protection of nucleobases

Org Biomol Chem. 2009 Feb 21;7(4):687-94. doi: 10.1039/b816831h. Epub 2009 Jan 7.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbamates / chemistry
  • DNA Probes / chemical synthesis*
  • Deoxyadenosines / chemistry
  • Deoxycytidine / chemistry
  • Hot Temperature
  • Nucleic Acid Precursors / chemical synthesis*

Substances

  • Carbamates
  • DNA Probes
  • Deoxyadenosines
  • Nucleic Acid Precursors
  • Deoxycytidine
  • carbamic acid