34361-60-9Relevant academic research and scientific papers
GLYCOSYL-INOSITOL DERIVATIVES III. SYNTHESIS OF HEXOSAMINE-INOSITOL-PHOSPHATES RELATED TO PUTATIVE INSULIN MEDIATORS
Berlin, William K.,Zhang, Wen-Sheng,Shen, T. Y.
, p. 1 - 20 (1991)
The disaccharides related to glycosyl phosphatidyl inositol anchors of membrane proteins, 4-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol-1-phosphate and 4-O-(2-amino-2-deoxy-α-D-galactopyranosyl)-D-chiro-inositol-1-phosphate, have been prepared from optically resolved myo-inositol derivatives.The chiro-inositol moiety was obtained by epimerization of a selectively blocked myo-inositol-triflate ester.The resolved inositols were subsequently phosphorylated to yield the disaccharide aglycones.The amino-sugar components were prepared by azidonitration of suitably protected glucal and galactal derivatives.The derived pyranosyl chlorides were then condensed with the inositol phosphates using silver triflate as the promoter.
Design and synthesis of biotinylated inositol phosphates relevant to the biotin-avidin techniques
Anraku, Kensaku,Inoue, Teruhiko,Sugimoto, Kenji,Morii, Takashi,Mori, Yasuo,Okamoto, Yoshinari,Otsuka, Masami
experimental part, p. 1822 - 1830 (2008/10/09)
Six bifunctional molecules containing biotin and various inositol phosphates were synthesized. These compounds were designed on the basis of X-ray structures of the complexes of d-myo-inositol 1,4,5-triphosphates (IP 3) and phospholipase C δ pleckstrin homology domain (PLCδ PH) considering the application to the biotin-avidin techniques. The building blocks of the inositol moiety were synthesized starting with optically resolved myo-inositol derivatives and assembled to the biotin linker through a phosphate linkage. The Royal Society of Chemistry.
Resolution of synthetically useful myo-inositol derivatives using the chiral auxiliary O-acetylmandelic acid
Sureshan, Kana M.,Kiyosawa, Yoko,Han, Fushe,Hyodo, Sayuri,Uno, Yuhki,Watanabe, Yutaka
, p. 231 - 241 (2007/10/03)
Efficient methods for the resolution of various myo-inositol derivatives have been developed using O-acetylmandelic acid (OAM) as the chiral auxiliary. Various methods of introduction of the chiral auxiliary have been compared. DCC mediated coupling betwe
First Total Synthesis of Mycothiol and Mycothiol Disulfide
Lee, Sungwon,Rosazza, John P. N.
, p. 365 - 368 (2007/10/03)
(Matrix presented) The first total synthesis of mycothiol and mycothiol disulfide was achieved by linking D-2,3,4,5,6-penta-O-acetyl-myo-inositol, O-(3,4,6-tri-O-acetyl)-2-azido-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate, and N,S-diacetyl-L-cysteine and deprotecting peracetylated mycothiol. The first full spectral characterization is reported for underivatized mycothiol. The structure of mycothiol was confirmed by spectral analysis of the known bimane derivative.
Synthesis of phosphatidylinositol mannosides (PIMs)
Stadelmaier, Andreas,Schmidt, Richard R.
, p. 2557 - 2569 (2007/10/03)
Two strategies towards the synthesis of phosphatidylinositol mannosides (PIMs) were elaborated which permit selective access to the O-1-, O-2-, and the O-6 position of the myo-inositol residue. Starting materials are 1,2:5,6- and 1,2:4,5-di-O-cyclohexylid
Synthesis of mycothiol, 1D-1-O-(2-[N-acetyl-L-cysteinyl]amino-2-deoxy-α-D-glucopyranosyl)-myo-inositol, principal low molecular mass thiol in the actinomycetes
Jardine,Spies, Hendrik S.C,Nkambule, Comfort M,Gammon, David W,Steenkamp, Daniel J
, p. 875 - 881 (2007/10/03)
Members of the actinomycetes produce 1D-1-O-(2-[N-acetyl-l-cysteinyl]amino-2-deoxy-α-D-glucopyranosyl)-myo-inositol or mycothiol 1 as principal low molecular mass thiol. Chemical synthesis of a biosynthetic precursor of mycothiol, the pseudo-disaccharide
The absolute configuration and optical purity of (-)- and (+)-1,2:4,5-di-O-cyclohexylidene-myo-inositols
Aneja,Aneja,Parra
, p. 17 - 18 (2007/10/02)
The absolute configurations of (-)- and (+)-1,2:4,5-di-O-cyclohexylidene-myo-inositols are derived as 1D- and 1L-1,2:4,5-di-O-cyclohexylidene-myo-inositols respectively, and are reverse of the most recent literature assignments.
Synthesis of meso-cyclohexa-3,5-diene-1,2-diol derivative from myo-inositol
Mereyala, Hari Babu,Pannala, Madhavi
, p. 2121 - 2124 (2007/10/02)
Synthesis of (meso)1,2-O-cyclohexylidene-cyclohexa-3,4-diene (4) in four steps from myo-inositol and its exclusive conversion to the vinylic epoxide 13 is described.
SYNTHESIS, POTENTIOMETRIC AND 31P-NMR INVESTIGATIONS OF THE IONIZATION STATE AND COMPLEXATION PROPERTIES OF INOSITOL-PHOSPHATES: BIOLOGICAL CONSEQUENCES
Schmitt, Laurent,Bortmann, Patrick,Spiess, Bernard,Schlewer, Gilbert
, p. 147 - 150 (2007/10/02)
The synthesis and the potentiometric studies of inositol-phosphates allow, particularly for Ins(1,4,5)P3, the correlation between the ionization state of the phosphate functions and the binding properties of the inositol-phosphates.
Synthesis and Some Properties of D-myo-Inositol 1,4,5-Tris(dihydrogen phosphate)
Ozaki, Shoichiro,Kondo, Yoshihisa,Shiotani, Naokazu,Ogasawara, Tomio,Watanabe, Yutaka
, p. 729 - 738 (2007/10/02)
Optically active myo-inositol 1,4,5-tris(dihydrogen phosphate) 1, which has now been recognized as a second messenger in a new intracellular signal transduction system, has been prepared starting from myo-inositol.The key step, phosphorylation of an adequately protected polyhydroxy derivative, was accomplished by three methods, among which a phosphoramidite method using a new phosphitylating agent, o-xylylene N,N-diethylphosphoramidite, gave the triphosphoric ester in quantitative yield.Optical resolution was effectively realized by derivatization into diastereoisomeric l-menthoxyacetic esters.NMR spectra and optical rotation are shown to depend on the pH of an aqueous solution of compound 1.
