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.
Phosphoinositide-based signaling processes are crucially important in intracellular signal transduction events. Inositol phosphate analogues have been useful in probing the structure-activity relationships between inositol phosphates and biomacromolecules, and in studying biological functions of newly found inositol phosphates. Thus, a systematic and ready access to inositol stereoisomers is highly desirable. And practical and convenient syntheses of conduritols and related compounds are also important because of their biological activities and their synthetic utilities in the preparation of other bioactive molecules. We herein report the first syntheses of all possible diastereomers of conduritol and various derivatives of eight inositol stereoisomers in high enantiopurity from myo-inositol, which involve efficient enzymatic resolution of the intermediates conduritol B and C derivatives, followed by oxidation-reduction or the Mitsunobu reaction, and cis-dihydroxylation in stereo- and regioselective manners.
Using a home-designed manually operated cylinder chamber and piston device, a reduced pressure headspace solid-phase microextraction gas chromatography/mass spectrometry (rpHSSPME-GC/MS) method, has been developed. By decreasing the pressure inside the sample chamber, the sensitivity of headspace SPME was improved remarkably, compared to normal atmospheric pressure conditions. With a solid sample, such as tobacco leaf, overall sensitivity was increased over 18 times at 200 mm Hg compared to atmospheric (760 mm Hg) conditions. Enhancement of SPME sensitivity was lower, but still significant, for an aqueous liquid sample, such as fresh black mulberry juice: extraction sensitivity was increased about 1.83 times (610 mm Hg), 2.14 times (380 mm Hg) and 3.37 times (60 mm Hg).Furthermore, more components were identified at lower extraction pressures. For example, 66 compounds were identified by rpHSSPME-GC/MS in the headspace of mulberry juice at 60 mm Hg, compared with 47 using standard (atmospheric pressure) HSSPME-GC/MS.
Poly(A) polymerase (PAP) play an essential role for maturation of mRNA by adding the adenylate residues at the 3' end. PAP functions are regulated through protein-protein interaction at its C-terminal region. In this study, cyclophilin A (CypA), a member of the peptidyl-prolyl cis-trans isomerase family, was identified as a partner protein interacting with the C-terminal region PAP. The interaction between PAP and CypA was inhibited by the immunosuppressive drug cyclosporine A. Deletion analysis revealed that the N-terminal 56 residues of CypA are sufficient for the interaction with PAP. Interestingly, we observed that PAP and CypA colocalize in the nucleus during SDF-1-induced chemotaxis, implying that CypA could be involved in the regulation of polyadenylation by PAP in the chemotactic cells.
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