5(6)-carboxyfluorescein revisited: new protecting group, separation of isomers, and their spectral properties on oligonucleotides.
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.
Kvach
Maksim V
MV
Institute of Physical Organic Chemistry, Surganova 13, 220072 Minsk, Belarus.
Tsybulsky
Dmitry A
DA
Ustinov
Alexey V
AV
Stepanova
Irina A
IA
Bondarev
Stanislav L
SL
Gontarev
Sergey V
SV
Korshun
Vladimir A
VA
Shmanai
Vadim V
VV
D002845:Chromatography; D003509:Cyclohexanecarboxylic Acids / Q000737:chemistry; D005452:Fluoresceins / Q000737:chemistry*; D007536:Isomerism; D009841:Oligonucleotides / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry; D010421:Pentanoic Acids / Q000737:chemistry; D013050:Spectrometry, Fluorescence
D003509:Cyclohexanecarboxylic Acids; D005452:Fluoresceins; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; D010421:Pentanoic Acids; C434331:phosphoramidite; C024098:6-carboxyfluorescein; C045132:4-carboxyfluorescein; C005566:pivalic acid