NDLI: Efficient and Scalable Synthesis of 4-Carboxy-Pennsylvania Green Methyl Ester: A Hydrophobic Building Block for Fluorescent Molecular Probes

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Efficient and Scalable Synthesis of 4-Carboxy-Pennsylvania Green Methyl Ester: A Hydrophobic Building Block for Fluorescent Molecular Probes

Content Provider	PubMed Central
Author	Woydziak, Zachary R. Fu, Liqiang Peterson, Blake R.
Abstract	Fluorinated fluorophores are valuable tools for studies of biological systems. However, amine-reactive single-isomer derivatives of these compounds are often very expensive. To provide an inexpensive alternative, we report a practical synthesis of 4-carboxy-Pennsylvania Green methyl ester. Derivatives of this hydrophobic fluorinated fluorophore, a hybrid of the dyes Oregon Green and Tokyo Green, are often cell permeable, enabling labeling of intracellular targets and components. Moreover, the low pKa of Pennsylvania Green (4.8) confers bright fluorescence in acidic cellular compartments such as endosomes, enhancing its utility for chemical biology investigations. To improve access to the key intermediate 2,7-difluoro-3,6-dihydroxyxanthen-9-one, we subjected bis-(2,4,5-trifluorophenyl)methanone to iterative nucleophilic aromatic substitution by hydroxide on scales of > 40 g. This intermediate was used to prepare over 15 grams of pure 4-carboxy-Pennsylvania Green methyl ester in 28% overall yield without requiring chromatography. This compound can be converted into the amine reactive N-hydroxysuccinimidyl ester in essentially quantitative yield for the synthesis of a wide variety of fluorescent molecular probes.
Related Links	http://dx.doi.org/10.1055/s-0033-1338535
Ending Page	164
Page Count	7
Starting Page	158
File Format	PDF
ISSN	00397881
e-ISSN	1437210X
Journal	Synthesis
Issue Number	2
Volume Number	46
Language	English
Publisher Date	2013-09-01
Access Restriction	Open
Subject Keyword	Organic Chemistry Catalysis Research in Higher Education
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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