Conformational probe: static quenching is reduced upon acid triggered ring flip of a myo-inositol derivative

Manikandan Kadirvel; Abdul Gbaj; David Mansell; Steven M. Miles; Biljana Arsic; Elena V. Bichenkova; Sally Freeman; Richard Bryce; Kenneth Douglas

doi:10.1016/j.tet.2008.03.045

Conformational probe: static quenching is reduced upon acid triggered ring flip of a myo-inositol derivative

Manikandan Kadirvel, Abdul Gbaj, David Mansell, Steven M. Miles, Biljana Arsic, Elena V. Bichenkova, Sally Freeman, Richard Bryce, Kenneth Douglas

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

Abstract

The aromatic rings in 4-O-dabsyl-6-O-dansyl-myo-inositol-1,3,5-orthoformate (6) participate in electron transfer causing static quenching as detected by the absence of fluorescence. Upon addition of acid, the orthoformate lock is cleaved, with subsequent conformational change of the myo-inositol ring from penta-axial to the more stable penta-equatorial chair, which causes some increase in fluorescence due to spatial separation of fluorophore and a quencher and reduction in static quenching. In the case of 4,6-O-bisdansyl-myo-inositol-1,3,5-orthoformate (3), the acid-induced removal of the orthoformate lock leads to substantial change of fluorescence following spatial separation of two dansyl groups. © 2008 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	5598-5603
Number of pages	5
Journal	Tetrahedron
Volume	64
Issue number	23
DOIs	https://doi.org/10.1016/j.tet.2008.03.045
Publication status	Published - 2 Jun 2008

Keywords

Conformation
Excimer
Exciplex
Fluorescent probe
Inositol
Static quenching
Trigger

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10.1016/j.tet.2008.03.045

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@article{948b0afa507f40efb554cb2343684dba,

title = "Conformational probe: static quenching is reduced upon acid triggered ring flip of a myo-inositol derivative",

abstract = "The aromatic rings in 4-O-dabsyl-6-O-dansyl-myo-inositol-1,3,5-orthoformate (6) participate in electron transfer causing static quenching as detected by the absence of fluorescence. Upon addition of acid, the orthoformate lock is cleaved, with subsequent conformational change of the myo-inositol ring from penta-axial to the more stable penta-equatorial chair, which causes some increase in fluorescence due to spatial separation of fluorophore and a quencher and reduction in static quenching. In the case of 4,6-O-bisdansyl-myo-inositol-1,3,5-orthoformate (3), the acid-induced removal of the orthoformate lock leads to substantial change of fluorescence following spatial separation of two dansyl groups. {\textcopyright} 2008 Elsevier Ltd. All rights reserved.",

keywords = "Conformation, Excimer, Exciplex, Fluorescent probe, Inositol, Static quenching, Trigger",

author = "Manikandan Kadirvel and Abdul Gbaj and David Mansell and Miles, {Steven M.} and Biljana Arsic and Bichenkova, {Elena V.} and Sally Freeman and Richard Bryce and Kenneth Douglas",

year = "2008",

month = jun,

day = "2",

doi = "10.1016/j.tet.2008.03.045",

language = "English",

volume = "64",

pages = "5598--5603",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier BV",

number = "23",

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TY - JOUR

T1 - Conformational probe: static quenching is reduced upon acid triggered ring flip of a myo-inositol derivative

AU - Kadirvel, Manikandan

AU - Gbaj, Abdul

AU - Mansell, David

AU - Miles, Steven M.

AU - Arsic, Biljana

AU - Bichenkova, Elena V.

AU - Freeman, Sally

AU - Bryce, Richard

AU - Douglas, Kenneth

PY - 2008/6/2

Y1 - 2008/6/2

N2 - The aromatic rings in 4-O-dabsyl-6-O-dansyl-myo-inositol-1,3,5-orthoformate (6) participate in electron transfer causing static quenching as detected by the absence of fluorescence. Upon addition of acid, the orthoformate lock is cleaved, with subsequent conformational change of the myo-inositol ring from penta-axial to the more stable penta-equatorial chair, which causes some increase in fluorescence due to spatial separation of fluorophore and a quencher and reduction in static quenching. In the case of 4,6-O-bisdansyl-myo-inositol-1,3,5-orthoformate (3), the acid-induced removal of the orthoformate lock leads to substantial change of fluorescence following spatial separation of two dansyl groups. © 2008 Elsevier Ltd. All rights reserved.

AB - The aromatic rings in 4-O-dabsyl-6-O-dansyl-myo-inositol-1,3,5-orthoformate (6) participate in electron transfer causing static quenching as detected by the absence of fluorescence. Upon addition of acid, the orthoformate lock is cleaved, with subsequent conformational change of the myo-inositol ring from penta-axial to the more stable penta-equatorial chair, which causes some increase in fluorescence due to spatial separation of fluorophore and a quencher and reduction in static quenching. In the case of 4,6-O-bisdansyl-myo-inositol-1,3,5-orthoformate (3), the acid-induced removal of the orthoformate lock leads to substantial change of fluorescence following spatial separation of two dansyl groups. © 2008 Elsevier Ltd. All rights reserved.

KW - Conformation

KW - Excimer

KW - Exciplex

KW - Fluorescent probe

KW - Inositol

KW - Static quenching

KW - Trigger

U2 - 10.1016/j.tet.2008.03.045

DO - 10.1016/j.tet.2008.03.045

M3 - Article

SN - 0040-4020

VL - 64

SP - 5598

EP - 5603

JO - Tetrahedron

JF - Tetrahedron

IS - 23

ER -

Conformational probe: static quenching is reduced upon acid triggered ring flip of a myo-inositol derivative

Abstract

Keywords

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