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Prometabolites of 5-Diphospho-myo-inositol Pentakisphosphate.
Journal article

Prometabolites of 5-Diphospho-myo-inositol Pentakisphosphate.

  • Pavlovic I Department of Chemistry, University of Zürich (UZH), Winterthurerstrasse 190, 8057 Zürich (Switzerland).
  • Thakor DT Department of Chemistry, University of Zürich (UZH), Winterthurerstrasse 190, 8057 Zürich (Switzerland).
  • Bigler L Department of Chemistry, University of Zürich (UZH), Winterthurerstrasse 190, 8057 Zürich (Switzerland).
  • Wilson MS LMCB, University College London (UK).
  • Laha D Center for Plant Molecular Biology, University of Tübingen (Germany).
  • Schaaf G Center for Plant Molecular Biology, University of Tübingen (Germany).
  • Saiardi A LMCB, University College London (UK).
  • Jessen HJ Department of Chemistry, University of Zürich (UZH), Winterthurerstrasse 190, 8057 Zürich (Switzerland). Henningjacob.jessen@chem.uzh.ch.
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  • 2015-05-28
Published in:
  • Angewandte Chemie (International ed. in English). - 2015
Inositol pyrophosphates
metabolism
protecting groups
second messengers
Animals
Arabidopsis
Brain
Cell Membrane Permeability
Dictyostelium
Humans
Inositol Phosphates
Liver
Rats
Signal Transduction
English Diphospho-myo-inositol phosphates (PP-InsP(y)) are an important class of cellular messengers. Thus far, no method for the transport of PP-InsP(y) into living cells is available. Owing to their high negative charge density, PP-InsP(y) will not cross the cell membrane. A strategy to circumvent this issue involves the generation of precursors in which the negative charges are masked with biolabile groups. A PP-InsP(y) prometabolite would require twelve to thirteen biolabile groups, which need to be cleaved by cellular enzymes to release the parent molecules. Such densely modified prometabolites of phosphate esters and anhydrides have never been reported to date. This study discloses the synthesis of such agents and an analysis of their metabolism in tissue homogenates by gel electrophoresis. The acetoxybenzyl-protected system is capable of releasing 5-PP-InsP5 in mammalian cell/tissue homogenates within a few minutes and can be used to release 5-PP-InsP5 inside cells. These molecules will serve as a platform for the development of fundamental tools required to study PP-InsP(y) physiology.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://folia.unifr.ch/global/documents/228925
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