Novel Saccharide-Photoinduced Electron Transfer Sensors Based on the Interaction of Boronic Acid and Amine

Tony D James, K R A S Sandanayake, R Iguchi, S Shinaki

Research output: Contribution to journalArticle

Abstract

Two boronic acid systems, monoboronic acid 3 and diboronic acid 8, were synthesized. When saccharides form cyclic boronate esters with these boronic acids, the Lewis acid-base interaction between the boronic acid moiety and tertiary amine is strengthened; when saccharides form cyclic boronate esters with boronic acids the acidity of the boronic acid is enhanced. The strength of this acid-base interaction modulates the photoinduced electron transfer (PET) from the amine to anthracene. Both of these compounds show increased fluoresecence at pH 7.77 through supression of the photoinduced electron transfer from nitrogen to anthracene on saccharide binding, a direct result of the stronger boron-nitrogen bond. Compound 3 shows the typical selectivity of monoboronic acids towards saccharides. Compound 8 which has a cleftlike structure is particularly selective and sensitive for, glucose due to the formation of an intramolecular 1:1 complex between the two boronic acids and the 1,2- and 4,6-hydroxyls of glucose. This is the first example in which ditopic recognition of monosaccharides is achieved in a PET sensor system.
Original languageEnglish
Pages (from-to)8982-8987
Number of pages6
JournalJournal of the American Chemical Society
Volume117
Issue number35
DOIs
Publication statusPublished - 1995

Fingerprint

Boronic Acids
Amines
Electrons
Acids
Sensors
Esters
Nitrogen
Lewis Bases
Glucose
Lewis Acids
Anthracene
Boron
Monosaccharides
Acidity
Hydroxyl Radical

Cite this

Novel Saccharide-Photoinduced Electron Transfer Sensors Based on the Interaction of Boronic Acid and Amine. / James, Tony D; Sandanayake, K R A S; Iguchi, R; Shinaki, S.

In: Journal of the American Chemical Society, Vol. 117, No. 35, 1995, p. 8982-8987.

Research output: Contribution to journalArticle

@article{e7b4d3183c4d415c963a1b93716552d9,
title = "Novel Saccharide-Photoinduced Electron Transfer Sensors Based on the Interaction of Boronic Acid and Amine",
abstract = "Two boronic acid systems, monoboronic acid 3 and diboronic acid 8, were synthesized. When saccharides form cyclic boronate esters with these boronic acids, the Lewis acid-base interaction between the boronic acid moiety and tertiary amine is strengthened; when saccharides form cyclic boronate esters with boronic acids the acidity of the boronic acid is enhanced. The strength of this acid-base interaction modulates the photoinduced electron transfer (PET) from the amine to anthracene. Both of these compounds show increased fluoresecence at pH 7.77 through supression of the photoinduced electron transfer from nitrogen to anthracene on saccharide binding, a direct result of the stronger boron-nitrogen bond. Compound 3 shows the typical selectivity of monoboronic acids towards saccharides. Compound 8 which has a cleftlike structure is particularly selective and sensitive for, glucose due to the formation of an intramolecular 1:1 complex between the two boronic acids and the 1,2- and 4,6-hydroxyls of glucose. This is the first example in which ditopic recognition of monosaccharides is achieved in a PET sensor system.",
author = "James, {Tony D} and Sandanayake, {K R A S} and R Iguchi and S Shinaki",
year = "1995",
doi = "10.1021/ja00140a013",
language = "English",
volume = "117",
pages = "8982--8987",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "35",

}

TY - JOUR

T1 - Novel Saccharide-Photoinduced Electron Transfer Sensors Based on the Interaction of Boronic Acid and Amine

AU - James, Tony D

AU - Sandanayake, K R A S

AU - Iguchi, R

AU - Shinaki, S

PY - 1995

Y1 - 1995

N2 - Two boronic acid systems, monoboronic acid 3 and diboronic acid 8, were synthesized. When saccharides form cyclic boronate esters with these boronic acids, the Lewis acid-base interaction between the boronic acid moiety and tertiary amine is strengthened; when saccharides form cyclic boronate esters with boronic acids the acidity of the boronic acid is enhanced. The strength of this acid-base interaction modulates the photoinduced electron transfer (PET) from the amine to anthracene. Both of these compounds show increased fluoresecence at pH 7.77 through supression of the photoinduced electron transfer from nitrogen to anthracene on saccharide binding, a direct result of the stronger boron-nitrogen bond. Compound 3 shows the typical selectivity of monoboronic acids towards saccharides. Compound 8 which has a cleftlike structure is particularly selective and sensitive for, glucose due to the formation of an intramolecular 1:1 complex between the two boronic acids and the 1,2- and 4,6-hydroxyls of glucose. This is the first example in which ditopic recognition of monosaccharides is achieved in a PET sensor system.

AB - Two boronic acid systems, monoboronic acid 3 and diboronic acid 8, were synthesized. When saccharides form cyclic boronate esters with these boronic acids, the Lewis acid-base interaction between the boronic acid moiety and tertiary amine is strengthened; when saccharides form cyclic boronate esters with boronic acids the acidity of the boronic acid is enhanced. The strength of this acid-base interaction modulates the photoinduced electron transfer (PET) from the amine to anthracene. Both of these compounds show increased fluoresecence at pH 7.77 through supression of the photoinduced electron transfer from nitrogen to anthracene on saccharide binding, a direct result of the stronger boron-nitrogen bond. Compound 3 shows the typical selectivity of monoboronic acids towards saccharides. Compound 8 which has a cleftlike structure is particularly selective and sensitive for, glucose due to the formation of an intramolecular 1:1 complex between the two boronic acids and the 1,2- and 4,6-hydroxyls of glucose. This is the first example in which ditopic recognition of monosaccharides is achieved in a PET sensor system.

UR - http://dx.doi.org/10.1021/ja00140a013

U2 - 10.1021/ja00140a013

DO - 10.1021/ja00140a013

M3 - Article

VL - 117

SP - 8982

EP - 8987

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 35

ER -