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

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

^*Corresponding author for this work

Chemical Engineering

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

7 Citations (Scopus)

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.

Original language	English
Pages (from-to)	5598-5603
Number of pages	6
Journal	Tetrahedron
Volume	64
Issue number	23
Early online date	15 Mar 2008
DOIs	https://doi.org/10.1016/j.tet.2008.03.045
Publication status	Published - 2 Jun 2008

Bibliographical note

Funding Information:
Overseas Research Scholarship and University of Manchester award to M.K. Research funded in part by the The Great Socialist People's Libyan Arab Jamahiriya (The Secretariat of Higher Education, Professor Akeel Hussain Akeel).

Keywords

Conformation
Excimer
Exciplex
Fluorescent probe
Inositol
Static quenching
Trigger

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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.",

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",

note = "Funding Information: Overseas Research Scholarship and University of Manchester award to M.K. Research funded in part by the The Great Socialist People's Libyan Arab Jamahiriya (The Secretariat of Higher Education, Professor Akeel Hussain Akeel).",

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T2 - 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

N1 - Funding Information: Overseas Research Scholarship and University of Manchester award to M.K. Research funded in part by the The Great Socialist People's Libyan Arab Jamahiriya (The Secretariat of Higher Education, Professor Akeel Hussain Akeel).

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.

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.

KW - Conformation

KW - Excimer

KW - Exciplex

KW - Fluorescent probe

KW - Inositol

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KW - Trigger

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DO - 10.1016/j.tet.2008.03.045

M3 - Article

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ER -

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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