137793-90-9Relevant academic research and scientific papers
Reducing the conformational flexibility of carbohydrates: Locking the 6-hydroxyl group by cyclopropanes
Brand, Christian,Granitzka, Markus,Stalke, Dietmar,Werz, Daniel B.
, p. 10782 - 10784 (2011/11/04)
The 6-hydroxyl group of hexopyranosides was stereochemically locked by the spiroannelation of a cyclopropane unit at C-5. The corresponding glucose and mannose derivatives were prepared and their behaviour in glycosidation reactions was studied.
Novel synthesis of enantiomerically pure natural inositols and their diastereoisomers
Takahashi,Kittaka,Ikegami
, p. 2705 - 2716 (2007/10/03)
The various inositol polyphosphates have been found to trigger many important biological processes. Although the knowledge of this phosphoinositide signaling system has been discovered in the past 10 years, many factors remain unclear. For this reason, there is an increased demand for supplies of D-myo-inositol and particularly of novel analogues to investigate these biological mechanisms in more detail. Herein, we report the efficient syntheses of all diastereoisomers of inositol starting with 6-O-acetyl-5-enopyranosides. Conversion of 6-O-acetyl-5-enopyranosides into the corresponding substituted cyclohexanones (Ferrier-II rearrangement) was found to proceed efficiently with a catalytic amount of palladium dichloride. Stereoselective reduction of β-hydroxy ketones obtained provided the precursors to all inositol diastereoisomers in good to excellent yields and with high stereoselectivities. Good accessibility of these enantiomerically pure inositol diastereoisomers results in the efficient syntheses of D-myo-inositol 1,4,5-trisphosphate and D-myo-inositol 1,3,4,5-tetrakisphosphate.
13C Labelling and electrospray mass spectrometry reveal a de novo route for inositol biosynthesis in Leishmania donovani parasite
Sahai, Parmeshwari,Chawla, Mamta,Vishwakarma, Ram A.
, p. 1283 - 1290 (2007/10/03)
In this paper we provide evidence for the presence of a de now route for myo-inositol biosynthesis in the protozoan parasite Leishmania donovani, by the application of 13C labelling and electrospray ionisation mass spectrometry (ESMS). For this myo-[1-13C]inositol is prepared from D-[6-13C]glucose and biosynthetically incorporated in the parasite promastigote cell culture. Biosynthetic phosphatidylinositol (PI) and its hydrolysis products glycero-PI and inositol are analysed by ESMS and the isotopomeric ratio determined. The incorporation experiments show substantial isotopic dilution, indicating the presence of myo-inositol 1-phosphate synthase (MIP synthase) enzyme in the parasite; this is further confirmed by incorporation of D-[6-13C]glucose in the parasite phosphatidylinositol. The Royal Society of Chemistry 2000.
Ready routes to key myo-inositol component of GPIs employing microbial arene oxidation or Ferrier reaction
Jia, Zhaozhong J.,Olsson, Lars,Fraser-Reid, Bert
, p. 631 - 632 (2007/10/03)
Microbial arene oxidation or Ferrier reaction of enol acetates provides versatile complementary routes that greatly facilitate preparation of inositol synthon(s) for GPI assembly.
Efficient syntheses of penta-hydroxylated cyclohexanones via PdCl2- mediated Ferrier-II reaction of 6-O-acetyl-5-enopyranosides
Takahashi, Hideyo,Kittaka, Hisae,Ikegami, Shiro
, p. 9703 - 9706 (2007/10/03)
The conversion of 6-O-acetyl-5-enopyranosides into fully oxygenated cyclohexanones was found to proceed efficiently with a catalytic amount of palladium chloride under neutral conditions. This method was proved to be superior in efficacy to the convention
