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

Research output: Contribution to journalArticlepeer-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 languageEnglish
Pages (from-to)5598-5603
Number of pages6
JournalTetrahedron
Volume64
Issue number23
Early online date15 Mar 2008
DOIs
Publication statusPublished - 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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