Synthesis and Structure of Cellular Mediators: Inositol Polyphosphate Diphosphates

J. R. Falck, K. Kishta Reddy, Jianhua Ye, Mourad Saady, Charles Mioskowski, Stephen B. Shears, Zheng Tan, Stephen Safrany

Research output: Contribution to journalArticle

25 Scopus citations

Abstract

The first total syntheses of 1-O-[(phosphonooxy)hydroxyphosphinyl]-2,3,4,5,6-pentakis-O-phosphono-D-myoinositol (10) and its antipode (11) were achieved from enantiopure 2,3:5,6-di-O-cyclohexylidene-D-myo-inositol (6). The critical pyrophosphate function was introduced, in the presence of flanking phosphate triesters, by mild LiCN-mediated cleavage of a mixed phosphate methyl ester, isolation of the resultant lithium salt, and addition to dibenzyl chlorophosphonate. The benzyl esters were removed by catalytic hydrogenolysis over Pd in t-BuOH/H2O in the presence of NaHCO3. Comparisons of synthetic and enzyme-devived pyrophosphates with two phosphatases suggests natural material has the stereochemical configuration in 10.

Original languageEnglish (US)
Pages (from-to)12172-12175
Number of pages4
JournalJournal of the American Chemical Society
Volume117
Issue number49
DOIs
StatePublished - Jan 1 1995

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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    Falck, J. R., Reddy, K. K., Ye, J., Saady, M., Mioskowski, C., Shears, S. B., Tan, Z., & Safrany, S. (1995). Synthesis and Structure of Cellular Mediators: Inositol Polyphosphate Diphosphates. Journal of the American Chemical Society, 117(49), 12172-12175. https://doi.org/10.1021/ja00154a017