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

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Abstract

The first total syntheses of 1-O-[(phosphonooxy)hydroxyphosphinyl]-2,3,4,5,6-pentakis-O-phosphono-D myo-inositol (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-derived 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 - Dec 13 1995

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Polyphosphates
Diphosphates
Inositol
Cellular Structures
Esters
Phosphates
Hydrogenolysis
Phosphatases
Lithium
Phosphoric Monoester Hydrolases
Enzymes
Salts
diphosphoric acid

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Falck, J. R., Reddy, K. K., Ye, J., Saady, M., Mioskowski, C., Shears, S. B., ... 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

Synthesis and structure of cellular mediators : Inositol polyphosphate diphosphates. / Falck, J. R.; Reddy, K. Kishta; Ye, Jianhua; Saady, Mourad; Mioskowski, Charles; Shears, Stephen B.; Tan, Zheng; Safrany, Stephen.

In: Journal of the American Chemical Society, Vol. 117, No. 49, 13.12.1995, p. 12172-12175.

Research output: Contribution to journalArticle

Falck, JR, Reddy, KK, Ye, J, Saady, M, Mioskowski, C, Shears, SB, Tan, Z & Safrany, S 1995, 'Synthesis and structure of cellular mediators: Inositol polyphosphate diphosphates', Journal of the American Chemical Society, vol. 117, no. 49, pp. 12172-12175. https://doi.org/10.1021/ja00154a017
Falck, J. R. ; Reddy, K. Kishta ; Ye, Jianhua ; Saady, Mourad ; Mioskowski, Charles ; Shears, Stephen B. ; Tan, Zheng ; Safrany, Stephen. / Synthesis and structure of cellular mediators : Inositol polyphosphate diphosphates. In: Journal of the American Chemical Society. 1995 ; Vol. 117, No. 49. pp. 12172-12175.
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