Divergent syntheses of all possible optically active regioisomers of myo-inositol tris- and tetrakisphosphates.
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 IP(n) is still lacking. As a continuing effort to our previously reported syntheses of all possible 39 optically inactive regioisomers of myo-inositol phosphates (IP(n); n = 1-6), we synthesized all possible optically active regioisomers of myo-IP(3) and myo-IP(4) using chiral IBz(3)s and IBz(2)s, 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 IBz(3) and six enantiomeric pairs of IBz(2), respectively. Phosphorylation of these intermediates by the phosphitylation and oxidation procedure gave the target products.
Chung
Sung-Kee
SK
Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science & Technology, Pohang 790-784, South Korea. skchung@postech.ac.kr
Kwon
Yong-Uk
YU
Shin
Jung-Han
JH
Chang
Young-Tae
YT
Lee
Changgook
C
Shin
Boo-Gyo
BG
Kim
Kyung-Cheol
KC
Kim
Mahn-Joo
MJ
D007202:Indicators and Reagents; D015544:Inositol 1,4,5-Trisphosphate / Q000138:chemical synthesis* / Q000737:chemistry; D007295:Inositol Phosphates / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D012964:Sodium; D013237:Stereoisomerism
D007202:Indicators and Reagents; D007295:Inositol Phosphates; D015544:Inositol 1,4,5-Trisphosphate; D012964:Sodium