Document Detail

Synthesis of 1L-chiro-inositol 2,3,5-trisphosphorothioate, the first partial agonist at the platelet myo-inositol 1,4,5-trisphosphate receptor.
MedLine Citation:
PMID:  7922136     Owner:  NLM     Status:  MEDLINE    
The synthesis of L-chiro-inositol 2,3,5-trisphosphorothioate, a novel analogue of the second messenger D-myo-inositol 1,4,5-trisphosphate has been accomplished from the natural product L-quebrachitol. Phosphitylation of (-)-1L-1,4,6-tri-O-benzoyl-chiro-inositol obtained from L-quebrachitol followed by sulfoxidation of the products gave (-)-1L-1,4,6-tri-O-benzoyl-chiro-inositol 2,3,5-tris[di(2-cyanoethyl) phosphorothioate], which was deblocked using sodium in liquid ammonia to give 1L-(-)-chiro-inositol 2,3,5-trisphosphorothioate. 1L-chiro-Inositol 2,3,5-trisphosphorothioate is a partial agonist in the release of intracellular Ca2+ from saponin-permeabilised platelets and is both a key tool for pharmacological dissection of the polyphosphoinositide pathway of cellular signalling and a lead compound for the design of small molecule Ins(1,4,5)P3 receptor antagonists.
C Liu; J al-Hafidh; J Westwick; B V Potter
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Publication Detail:
Type:  In Vitro; Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  2     ISSN:  0968-0896     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  1994 Apr 
Date Detail:
Created Date:  1994-11-10     Completed Date:  1994-11-10     Revised Date:  2007-07-18    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  253-7     Citation Subset:  IM    
School of Pharmacy & Pharmacology, University of Bath, U.K.
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MeSH Terms
Blood Platelets / drug effects*,  metabolism*
Calcium / metabolism
Calcium Channels / chemistry*
Inositol 1,4,5-Trisphosphate / analogs & derivatives*,  chemical synthesis,  chemistry,  pharmacology
Inositol 1,4,5-Trisphosphate Receptors
Organothiophosphorus Compounds / chemical synthesis*,  chemistry,  pharmacology
Receptors, Cytoplasmic and Nuclear / chemistry*
Second Messenger Systems
Reg. No./Substance:
0/Calcium Channels; 0/Inositol 1,4,5-Trisphosphate Receptors; 0/Organothiophosphorus Compounds; 0/Receptors, Cytoplasmic and Nuclear; 0/inositol 2,3,5-trisphosphorothioate; 7440-70-2/Calcium; 85166-31-0/Inositol 1,4,5-Trisphosphate

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