Literature DB >> 16832513

Regioselective hydrolysis of myo-inositol 1,3,5-orthobenzoate via a 1,2-bridged 2'-phenyl-1',3'-dioxolan-2'-ylium ion provides a rapid route to the anticancer agent Ins(1,3,4,5,6)P5.

Himali Y Godage1, Andrew M Riley, Timothy J Woodman, Barry V L Potter.   

Abstract

Acid hydrolysis of myo-inositol 1,3,5-orthobenzoate leads regioselectively to 2-O-benzoyl-myo-inositol via a 1,2-bridged 2'-phenyl-1',3'-dioxolan-2'-ylium ion observed by 1H and 13C NMR spectroscopy, providing the precursor for a highly efficient route to the anticancer agent myo-inositol 1,3,4,5,6-pentakisphosphate.

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Year:  2006        PMID： 16832513     DOI： 10.1039/b605392k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  8 in total

Review 1.  The "Other" Inositols and Their Phosphates: Synthesis, Biology, and Medicine (with Recent Advances in myo-Inositol Chemistry).

Authors:  Mark P Thomas; Stephen J Mills; Barry V L Potter
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-22       Impact factor: 15.336

2.  Inositol polyphosphates intersect with signaling and metabolic networks via two distinct mechanisms.

Authors:  Mingxuan Wu; Lucy S Chong; David H Perlman; Adam C Resnick; Dorothea Fiedler
Journal:  Proc Natl Acad Sci U S A       Date:  2016-10-19       Impact factor: 11.205

3.  Synthesis and characterization of non-hydrolysable diphosphoinositol polyphosphate second messengers.

Authors:  Mingxuan Wu; Barbara E Dul; Alexandra J Trevisan; Dorothea Fiedler
Journal:  Chem Sci       Date:  2013-01       Impact factor: 9.825

4.  The behaviour of inositol 1,3,4,5,6-pentakisphosphate in the presence of the major biological metal cations.

Authors:  Nicolás Veiga; Julia Torres; Himali Y Godage; Andrew M Riley; Sixto Domínguez; Barry V L Potter; Alvaro Díaz; Carlos Kremer
Journal:  J Biol Inorg Chem       Date:  2009-05-05       Impact factor: 3.358

5.  Regioselective opening of myo-inositol orthoesters: mechanism and synthetic utility.

Authors:  Himali Y Godage; Andrew M Riley; Timothy J Woodman; Mark P Thomas; Mary F Mahon; Barry V L Potter
Journal:  J Org Chem       Date:  2013-03-05       Impact factor: 4.354

6.  Synthetic inositol phosphate analogs reveal that PPIP5K2 has a surface-mounted substrate capture site that is a target for drug discovery.

Authors:  Huanchen Wang; Himali Y Godage; Andrew M Riley; Jeremy D Weaver; Stephen B Shears; Barry V L Potter
Journal:  Chem Biol       Date:  2014-04-24

7.  A Small Molecule Inhibitor of PDK1/PLCγ1 Interaction Blocks Breast and Melanoma Cancer Cell Invasion.

Authors:  Claudio Raimondi; Veronique Calleja; Riccardo Ferro; Alessandro Fantin; Andrew M Riley; Barry V L Potter; Caroline H Brennan; Tania Maffucci; Banafshé Larijani; Marco Falasca
Journal:  Sci Rep       Date:  2016-05-20       Impact factor: 4.379

8.  A novel inhibitor of the PI3K/Akt pathway based on the structure of inositol 1,3,4,5,6-pentakisphosphate.

Authors:  M Falasca; D Chiozzotto; H Y Godage; M Mazzoletti; A M Riley; S Previdi; B V L Potter; M Broggini; T Maffucci
Journal:  Br J Cancer       Date:  2010-01-05       Impact factor: 7.640
  8 in total

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