5(6)-carboxyfluorescein revisited: new protecting group, separation of isomers, and their spectral properties on oligonucleotides

  • Bioconjug Chem. 2007 Sep-Oct;18(5):1691-6. doi: 10.1021/bc7001874.
Maksim V Kvach  1 ,  Dmitry A Tsybulsky ,  Alexey V Ustinov ,  Irina A Stepanova ,  Stanislav L Bondarev ,  Sergey V Gontarev ,  Vladimir A Korshun ,  Vadim V Shmanai
Affiliations
  • 1. Institute of Physical Organic Chemistry, Surganova 13, 220072 Minsk, Belarus.
PMID: 17696491 DOI: 10.1021/bc7001874
Abstract

Pentafluorophenyl esters of 5- and 6-carboxyfluorescein-3',6'-O-dipivalate can be easily separated in multigram quantities by column chromatography. The individual isomers were converted into stable phosphoramidites suitable for oligonucleotide synthesis. The use of the cyclohexylcarbonyl (Chc) protecting group instead of pivaloyl (Piv) facilitates the separation of isomers. The fluorescence spectra of 5- and 6-carboxyfluoresceins on oligonucleotides were compared.

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