Regioselective synthesis of 1,3,5-13 C3 and 2,4-13 C2-labeled 2-deoxyribonolactones

Paul J. Hatala, James Kallmerten, Philip N Borer

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

The synthesis of 1,3,5-13 C3- and 2,4-13 C2-labeled 5-0-bromobenzyl2-deoxyribonolactones 2, precursors to 13C-enriched nucleoside phosphoramidites for solid-phase synthesis of DNA oligonucletides, is described. An equimolar combination of these two multiply labeled lactones affords a "population-labeled" mixture of isotopomers which exhibits an approximately 50-fold increase in the sensitivity of 13C-NMR compared to natural abundance measurements. The 13C-13 C 2-bond and 4-bond coupling constants are reported for the lactones; all are < 2Hz, confirming that this labeling scheme should be especially useful for NMR-relaxation measurements.

Original languageEnglish (US)
Pages (from-to)1961-1973
Number of pages13
JournalNucleosides, Nucleotides and Nucleic Acids
Volume20
Issue number12
DOIs
StatePublished - Dec 31 2001

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Genetics

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