Syntheses of (2')3'-15N-amino-(2')3'-deoxyguanosine and determination of their pKa values by 15N NMR spectroscopy

Org Lett. 2007 Aug 2;9(16):3057-60. doi: 10.1021/ol071129h. Epub 2007 Jul 13.

Abstract

2'-Amino-2'-deoxyguanosine and 3'-amino-3'-deoxyguanosine are valuable probes for investigating the metal ion interactions at the active site of the group I ribozyme. However, these experiments require a thorough understanding of the protonation state of the amino group at a specific pH. Here, we describe the first syntheses of 2'-15N-amino-2'-deoxyadenosine, 2'-15N-amino-2'-deoxyguanosine, and 3'-15N-amino-3'-deoxyguanosine. The 15N-enriched nucleus allows convenient and accurate determination of the amine pKa by 15N NMR.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding Sites
  • Deoxyguanosine* / analogs & derivatives
  • Deoxyguanosine* / chemical synthesis
  • Deoxyguanosine* / chemistry
  • Deoxyguanosine* / pharmacokinetics
  • Hydrogen-Ion Concentration
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • RNA, Catalytic / chemistry

Substances

  • RNA, Catalytic
  • Deoxyguanosine