Facile Large-Scale Synthesis of 5- and 6-Carboxyfluoresceins: Application for the Preparation of New Fluorescent Dyes

A series of fluorescein dyes have been prepared from a common precursor through a very simple synthetic procedure, giving access to important precursors for fluorescent probes. The method has proven an efficient access to regioisomerically pure 5‐ and 6‐carboxyfluoresceins on a large scale, in good...

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Bibliographic Details
Published in:European journal of organic chemistry 2015-11, Vol.2015 (33), p.7301-7309
Main Authors: Hammershøj, Peter, Kumar, E. K. Pramod, Harris, Pernille, Andresen, Thomas L., Clausen, Mads H.
Format: Article
Language:English
Subjects:
Chromophores
Dyes
Fluorescent probes
Polycycles
Synthetic methods
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Summary:A series of fluorescein dyes have been prepared from a common precursor through a very simple synthetic procedure, giving access to important precursors for fluorescent probes. The method has proven an efficient access to regioisomerically pure 5‐ and 6‐carboxyfluoresceins on a large scale, in good yields, and with high regioisomeric purity. Furthermore, we have applied the method to the development of a new type of mixed fluorescein derivatives of 5‐carboxyfluorescein. We have demonstrated the scope of the procedure by synthesizing a new type of double chromophore within the fluoro‐Jade family. The right intermediate for everything. A new method with a very flexible design strategy has been used to synthesize regioisomerically pure 5‐ and 6‐carboxyfluoresceins and also applied to the synthesis of known chromophores of carboxyfluorescein. This approach, applicable to a range of fluorescein derivatives, directly produces chromophores suitable for conjugation and use as imaging probes.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201501013