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Lim, Mi Hee
MetalloNeuroChemistry Lab (MNCL)
Research Interests
  • Neurodegenerative disease, small molecule design, network between metal, proteins, and ROS

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Synthesis of isomerically pure carboxylate- and sulfonate-substituted xanthene fluorophores

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Title
Synthesis of isomerically pure carboxylate- and sulfonate-substituted xanthene fluorophores
Author
Woodroofe, CCLim, Mi HeeBu, WMLippard, SJ
Keywords
Asymmetric fluorescein carboxylate; Dibromofluoran; Fluorescein sulfonic acid; Fractional crystallization; Isomer resolution; Rhodamine carboxylate
Issue Date
2005-03
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Citation
TETRAHEDRON, v.61, no.12, pp.3097 - 3105
Abstract
Xanthene-based fluorophores such as fluorescein and rhodamine are typically prepared by acid-catalyzed condensation of the appropriate resorcinol or 3-aminophenol with phthalic anhydride. Condensation of substituted phthalic anhydride species results in functionalized fluorophores that are formed as mixed isomers. Crystallization approaches to isomer separation have been reported elsewhere for symmetric fluorescein carboxylates. We describe crystallization-based separation of protected fluorescein sulfonates and coupling conditions to form sulfonamides, precursors for carboxylate-substituted rhodamines, and precursors for asymmetrically substituted fluoresceins and rhodafluors.
URI
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DOI
10.1016/j.tet.2005.01.024
ISSN
0040-4020
Appears in Collections:
PHY_Journal Papers
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