Divergent syntheses of all possible optically active regioisomers of myo-inositol tris- and tetrakisphosphates

Sung Kee Chung, Yong Uk Kwon, Jung Han Shin, Young Tae Chang, Changgook Lee, Boo Gyo Shin, Kyung Cheol Kim, Mahn Joo Kim

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23 Scopus citations


Since the discovery of D-myo-inositol 1,4,5-trisphosphate, which plays a pivotal role as a second messenger in transmembrane signaling, the scope of the phosphoinositide-based signaling processes has been continually expanding. However, the clear understanding of the molecular signal transduction mechanisms including the functions of newly found IPn is still lacking. As a continuing effort to our previously reported syntheses of all possible 39 optically inactive regioisomers of myoinositol phosphates (IPn; n = 1-6), we synthesized all possible optically active regioisomers of myo-IP3 and myo-IP4 using chiral IBz3s and IBz2s, respectively. A series of procedures involving CRL-catalyzed enzymatic resolution of racemic 1,2:5,6-di-O-isopropylidene-myo-inositol and base-catalyzed benzoyl migration in tri- and dibenzoyl-isopropylidene-myo-inositol afforded eight enantiomeric pairs of IBz3 and six enantiomeric pairs of IBz2, respectively. Phosphorylation of these intermediates by the phosphitylation and oxidation procedure gave the target products.

Original languageEnglish
Pages (from-to)5626-5637
Number of pages12
JournalJournal of Organic Chemistry
Issue number16
StatePublished - 9 Aug 2002


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