Synthesis and carbohydrate binding studies of fluorescent alpha-amidoboronic acids and the corresponding bisboronic acids.

Bioorganic & Medicinal Chemistry
Shan JinBinghe Wang

Abstract

Fluorescent boronic acids are very useful for the design and synthesis of carbohydrate sensors. In an earlier communication, we first described the effort of developing water soluble fluorescent alpha-amidoboronic acids, which change fluorescence upon sugar binding. In this report, we describe a general method of functionalizing such boronic acids and their applications in the preparation of bis-alpha-amidoboronic acids with significantly enhanced binding for oligosaccharides as compared to their monoboronic acid counterparts. The advantages of good water solubility, easy modification to generate diversity, and modularity in synthesis will make alpha-amidoboronic acids very useful building blocks for future synthesis of boronic acid-based fluorescent sensors.

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Citations

Sep 21, 2016·Organic Letters·Daiki NishikawaMasahiro Miura
Dec 3, 2016·Chemical Communications : Chem Comm·Wenlei ZhaiJohn S Fossey
Jan 21, 2017·Chemical Communications : Chem Comm·Graham E GarrettMark S Taylor
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Dec 13, 2019·The Analyst·Zhancun BianZhongyu Wu
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May 15, 2015·Chemical Reviews·Xiaolong Sun, Tony D James
Sep 30, 2021·Chemical Society Reviews·Wenbo MingTodd B Marder

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