454428-84-3Relevant academic research and scientific papers
Divergent syntheses of all possible optically active regioisomers of myo-inositol tris- and tetrakisphosphates
Chung, Sung-Kee,Kwon, Yong-Uk,Shin, Jung-Han,Chang, Young-Tae,Lee, Changgook,Shin, Boo-Gyo,Kim, Kyung-Cheol,Kim, Mahn-Joo
, p. 5626 - 5637 (2007/10/03)
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.
