A dual role of phenylboronic acid as a receptor for carbohydrates as well as a quencher for neighboring pyrene fluorophore

Lok Nath Neupane; Chuda Raj Lohani; Jeongho Kim; Keun Hyeung Lee

doi:10.1016/j.tet.2013.11.023

A dual role of phenylboronic acid as a receptor for carbohydrates as well as a quencher for neighboring pyrene fluorophore

Lok Nath Neupane, Chuda Raj Lohani, Jeongho Kim, Keun Hyeung Lee

Inha University

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

Abstract

A simple amino acid based compound (1) containing a phenyl boronic group and pyrene fluorophore showed an enhanced fluorescence in aqueous solutions at physiological pH through suppression of the photoinduced electron transfer from pyrene to boronic acid on carbohydrate binding. The compound exhibited an interesting fluorescence change depending on pH with decreased emission intensity at acidic pH but enhanced emission intensity at basic pH unlike the fluorescent carbohydrate chemosensors using a PET process with amine and aryl-boronic acid. We have characterized a dual role of phenylboronic acid as a receptor for carbohydrates as well as a quencher for the fluorescence of pyrene fluorophore.

Original language	English
Pages (from-to)	11057-11063
Number of pages	7
Journal	Tetrahedron
Volume	69
Issue number	52
DOIs	https://doi.org/10.1016/j.tet.2013.11.023
State	Published - 30 Dec 2013

Bibliographical note

Funding Information:
This work was supported by a grant ( 2012R1AB3000574 ) from the National Research Foundation and a grant ( 201200054 0013 ) from the Korea Environmental Industry and Technology Institute .

Keywords

Carbohydrate
Chemosensor
Phenylboronic acid
Sugar
Turn on

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10.1016/j.tet.2013.11.023

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title = "A dual role of phenylboronic acid as a receptor for carbohydrates as well as a quencher for neighboring pyrene fluorophore",

abstract = "A simple amino acid based compound (1) containing a phenyl boronic group and pyrene fluorophore showed an enhanced fluorescence in aqueous solutions at physiological pH through suppression of the photoinduced electron transfer from pyrene to boronic acid on carbohydrate binding. The compound exhibited an interesting fluorescence change depending on pH with decreased emission intensity at acidic pH but enhanced emission intensity at basic pH unlike the fluorescent carbohydrate chemosensors using a PET process with amine and aryl-boronic acid. We have characterized a dual role of phenylboronic acid as a receptor for carbohydrates as well as a quencher for the fluorescence of pyrene fluorophore.",

keywords = "Carbohydrate, Chemosensor, Phenylboronic acid, Sugar, Turn on",

author = "Neupane, {Lok Nath} and Lohani, {Chuda Raj} and Jeongho Kim and Lee, {Keun Hyeung}",

note = "Funding Information: This work was supported by a grant ( 2012R1AB3000574 ) from the National Research Foundation and a grant ( 201200054 0013 ) from the Korea Environmental Industry and Technology Institute . ",

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doi = "10.1016/j.tet.2013.11.023",

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AU - Neupane, Lok Nath

AU - Lohani, Chuda Raj

AU - Kim, Jeongho

AU - Lee, Keun Hyeung

N1 - Funding Information: This work was supported by a grant ( 2012R1AB3000574 ) from the National Research Foundation and a grant ( 201200054 0013 ) from the Korea Environmental Industry and Technology Institute .

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Y1 - 2013/12/30

N2 - A simple amino acid based compound (1) containing a phenyl boronic group and pyrene fluorophore showed an enhanced fluorescence in aqueous solutions at physiological pH through suppression of the photoinduced electron transfer from pyrene to boronic acid on carbohydrate binding. The compound exhibited an interesting fluorescence change depending on pH with decreased emission intensity at acidic pH but enhanced emission intensity at basic pH unlike the fluorescent carbohydrate chemosensors using a PET process with amine and aryl-boronic acid. We have characterized a dual role of phenylboronic acid as a receptor for carbohydrates as well as a quencher for the fluorescence of pyrene fluorophore.

AB - A simple amino acid based compound (1) containing a phenyl boronic group and pyrene fluorophore showed an enhanced fluorescence in aqueous solutions at physiological pH through suppression of the photoinduced electron transfer from pyrene to boronic acid on carbohydrate binding. The compound exhibited an interesting fluorescence change depending on pH with decreased emission intensity at acidic pH but enhanced emission intensity at basic pH unlike the fluorescent carbohydrate chemosensors using a PET process with amine and aryl-boronic acid. We have characterized a dual role of phenylboronic acid as a receptor for carbohydrates as well as a quencher for the fluorescence of pyrene fluorophore.

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KW - Phenylboronic acid

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DO - 10.1016/j.tet.2013.11.023

M3 - Article

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ER -

A dual role of phenylboronic acid as a receptor for carbohydrates as well as a quencher for neighboring pyrene fluorophore

Abstract

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