Sulfonation of 3,3'-DiformylBINOL for Enantioselective Fluorescent Recognition of Amino Acids in Water

Chemistry : a European Journal
Lin PuXiaoqi Yu

Abstract

Reaction of (R)-3,3'-diformyl-1,1'-bi-2-naphthol with concentrated sulfuric acid gives the corresponding 6,6'-disulfonated compound (R)- 2 selectively. This provides a simple and efficient method to convert a water insoluble compound to a water soluble fluorescent probe. It is found that (R)- 2 in combination with Zn2+ shows highly enantioselective fluorescent response toward various amino acids in the aqueous HEPES buffer solution at pH = 7.4. For example, an enantioselective fluorescence enhancement ratio [ef = ΔID /ΔIL] up to 35.8 is observed for the recognition of asparagine. NMR and mass spectroscopic investigations are conducted to explore the reaction of (R)- 2 with asparagine.

References

Mar 11, 2004·Chemical Reviews·Lin Pu
Apr 26, 2011·Topics in Current Chemistry·Alessandro AccettaRosangela Marchelli
Jul 30, 2011·Chemical Society Reviews·Ying Zhou, Juyoung Yoon
Sep 6, 2011·Chemical Society Reviews·Diana LeungEric V Anslyn
Mar 2, 2013·Chemical Communications : Chem Comm·Fengyan SongChengjian Zhu
Feb 7, 2014·Chemical Reviews·Xin ZhangJuyoung Yoon
Jul 31, 2018·Journal of the American Chemical Society·Brenden T HerreraChristian Wolf

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Citations

Jun 9, 2021·Luminescence : the Journal of Biological and Chemical Luminescence·Hiroki TokunagaMakoto Miyasaka
Jun 25, 2021·The Journal of Organic Chemistry·Yu ChenLin Pu

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