ArticleChembiochem : a European journal of chemical biology2006
scyllo-inositol pentakisphosphate as an analogue of myo-inositol 1,3,4,5,6-pentakisphosphate: chemical synthesis, physicochemistry and biological applications.
Article in Chembiochem : a European journal of chemical biology, 2006. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 29 citations in OpenAlex.
- Inositol Thiophosphates as Inhibitors of Mammalian, Plant, and Fungal Phytases.ACS chemical biology · 2026Article
- Substrate promiscuity of inositol 1,4,5-trisphosphate kinase driven by structurally-modified ligands and active site plasticity.Nature communications · 2024Article
- Biochemical and structural characterization of an inositol pyrophosphate kinase from a giant virus.The EMBO journal · 2024Article
- Modulation of the substrate specificity of the kinase PDK1 by distinct conformations of the full-length protein.Science signaling · 2023Article
- One Scaffold, Two Conformations: The Ring-Flip of the Messenger InsPBiomolecules · 2023Article
- Novel Substrates for Kinases Involved in the Biosynthesis of Inositol Pyrophosphates and Their Enhancement of ATPase Activity of a Kinase.Molecules (Basel, Switzerland) · 2021Article
- Inositol hexakisphosphate increases the size of platelet aggregates.Biochemical pharmacology · 2019Article
- Simple synthesis ofPlant and soil · 2018Article
- Cellular Cations Control Conformational Switching of Inositol Pyrophosphate Analogues.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Insights into the activation mechanism of class I HDAC complexes by inositol phosphates.Nature communications · 2016Article
- The "Other" Inositols and Their Phosphates: Synthesis, Biology, and Medicine (with Recent Advances in myo-Inositol Chemistry).Angewandte Chemie (International ed. in English) · 2016Review
- Inframolecular acid-base and coordination properties towards Na(+) and Mg(2+) of myo-inositol 1,3,4,5,6-pentakisphosphate: a structural approach to biologically relevant species.Dalton transactions (Cambridge, England : 2003) · 2013Article
- Synthesis and characterization of non-hydrolysable diphosphoinositol polyphosphate second messengers.Chemical science · 2013Article
- Fibrinogen - a possible extracellular target for inositol phosphates.Messenger (Los Angeles, Calif. : Print) · 2012Article
- The behaviour of inositol 1,3,4,5,6-pentakisphosphate in the presence of the major biological metal cations.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2009Article
- Synthetic partial agonists reveal key steps in IP3 receptor activation.Nature chemical biology · 2009Article
- Purification, sequencing, and molecular identification of a mammalian PP-InsP5 kinase that is activated when cells are exposed to hyperosmotic stress.The Journal of biological chemistry · 2007Article
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Authors and funding
10 authors at 4 institutions in 4 countries.
Funding
Abstract
myo-Inositol 1,3,4,5,6-pentakisphosphate (Ins(1,3,4,5,6)P(5)), an inositol polyphosphate of emerging significance in cellular signalling, and its C-2 epimer scyllo-inositol pentakisphosphate (scyllo-InsP(5)) were synthesised from the same myo-inositol-based precursor. Potentiometric and NMR titrations show that both pentakisphosphates undergo a conformational ring-flip at higher pH, beginning at pH 8 for scyllo-InsP(5) and pH 9 for Ins(1,3,4,5,6)P(5). Over the physiological pH range, however, the conformation of the inositol rings and the microprotonation patterns of the phosphate groups in Ins(1,3,4,5,6)P(5) and scyllo-InsP(5) are similar. Thus, scyllo-InsP(5) should be a useful tool for identifying biologically relevant actions of Ins(1,3,4,5,6)P(5), mediated by specific binding sites, and distinguishing them from nonspecific electrostatic effects. We also demonstrate that, although scyllo-InsP(5) and Ins(1,3,4,5,6)P(5) are both hydrolysed by multiple inositol polyphosphate phosphatase (MINPP), scyllo-InsP(5) is not dephosphorylated by PTEN or phosphorylated by Ins(1,3,4,5,6)P(5) 2-kinases. This finding both reinforces the value of scyllo-InsP(5) as a biological control and shows that the axial 2-OH group of Ins(1,3,4,5,6)P(5) plays a part in substrate recognition by PTEN and the Ins(1,3,4,5,6)P(5) 2-kinases.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.