- GLYCOSYL-INOSITOL DERIVATIVES III. SYNTHESIS OF HEXOSAMINE-INOSITOL-PHOSPHATES RELATED TO PUTATIVE INSULIN MEDIATORS
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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.
- Berlin, William K.,Zhang, Wen-Sheng,Shen, T. Y.
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- Design and synthesis of biotinylated inositol phosphates relevant to the biotin-avidin techniques
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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.
- Anraku, Kensaku,Inoue, Teruhiko,Sugimoto, Kenji,Morii, Takashi,Mori, Yasuo,Okamoto, Yoshinari,Otsuka, Masami
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experimental part
p. 1822 - 1830
(2008/10/09)
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- Resolution of synthetically useful myo-inositol derivatives using the chiral auxiliary O-acetylmandelic acid
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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
- Sureshan, Kana M.,Kiyosawa, Yoko,Han, Fushe,Hyodo, Sayuri,Uno, Yuhki,Watanabe, Yutaka
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p. 231 - 241
(2007/10/03)
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- First Total Synthesis of Mycothiol and Mycothiol Disulfide
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(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.
- Lee, Sungwon,Rosazza, John P. N.
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p. 365 - 368
(2007/10/03)
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- Synthesis of phosphatidylinositol mannosides (PIMs)
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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
- Stadelmaier, Andreas,Schmidt, Richard R.
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p. 2557 - 2569
(2007/10/03)
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- 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
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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
- Jardine,Spies, Hendrik S.C,Nkambule, Comfort M,Gammon, David W,Steenkamp, Daniel J
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p. 875 - 881
(2007/10/03)
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- The absolute configuration and optical purity of (-)- and (+)-1,2:4,5-di-O-cyclohexylidene-myo-inositols
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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.
- Aneja,Aneja,Parra
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- Synthesis of meso-cyclohexa-3,5-diene-1,2-diol derivative from myo-inositol
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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.
- Mereyala, Hari Babu,Pannala, Madhavi
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p. 2121 - 2124
(2007/10/02)
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- SYNTHESIS, POTENTIOMETRIC AND 31P-NMR INVESTIGATIONS OF THE IONIZATION STATE AND COMPLEXATION PROPERTIES OF INOSITOL-PHOSPHATES: BIOLOGICAL CONSEQUENCES
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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.
- Schmitt, Laurent,Bortmann, Patrick,Spiess, Bernard,Schlewer, Gilbert
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p. 147 - 150
(2007/10/02)
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- A Chiral Synthesis of D-myo-Inositol 1-Phosphate Starting from L-Quebrachitol
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A naturally occurring optically active cyclitol, L-quebrachitol (1L-2-O-methyl-chiro-inositol), was stereoselectively transformed into myo-inositol derivatives via an oxidation-reduction process.The methyl ether was cleaved chemoselectively with AlCl3NaI
- Akiyama, Takahiko,Takechi, Naoto,Ozaki, Shoichiro,Shiota, Kenji
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p. 366 - 372
(2007/10/02)
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- Synthesis and Some Properties of D-myo-Inositol 1,4,5-Tris(dihydrogen phosphate)
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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.
- Ozaki, Shoichiro,Kondo, Yoshihisa,Shiotani, Naokazu,Ogasawara, Tomio,Watanabe, Yutaka
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p. 729 - 738
(2007/10/02)
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- Synthesis of racemic 3-methylphosphonate analogues of myo-inositol 3,4-bis- and 1,3,4-trisphosphate
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The partially benzyl protected myo-inositol derivatives 11a and 11b, the C-4 and C-1,4 hydroxyl function(s) of which are protected with temporary trans-prop-1-enyl protecting group(s), were readily converted into the respective title compounds 18a and 18b by sequential methylphosphonylation, mild cleavage of the trans-prop-1-enyl group(s), phosphorylation and removal of all permanent benzyl protecting groups.
- Dreef,Tuinman,Lefeber,Elie,Van Der Marel,Van Boom
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p. 4709 - 4722
(2007/10/02)
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- The synthesis of DL-1-(hexadecanoyloxy)methyl- and 1-O-hexadecanoyl-inositols as potential inhibitors of phospholipase C
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The synthesis of racemic analogues of phosphatidylinositol (PI) and phosphatidylinositol 4,5-bisphosphate (PIP2) starting from myo-inositol is described. Inositol derivatives with and without homologation at C(1) and with and without ionic grou
- James,Massy,Wyss
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p. 1037 - 1057
(2007/10/02)
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- THE TOTAL SYNTHESIS OF myo-INOSITOL POLYPHOSPHATES
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Total synthesis of the individual enentiomers of myo-inositol 4-phosphate (15), myo-inositol 1,4-biphosphate (2) and myo-inositol 1,4,5-triphosphate (1), together with syntheses of racemic myo-inositol 1,3,4-triphosphate (4) and myo-inositol 2,4,5-triphos
- Vacca, Joseph P.,deSolms, S. Jane,Huff, Joel R.,Billington, David C.,Baker, Raymond,et al.
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p. 5679 - 5702
(2007/10/02)
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- SYNTHESIS OF RACEMIC MYO-INOSITOL 1,3,4-TRIPHOSPHATE VIA A PHOSPHITE-TRIESTER APPROACH
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Phosphitylation of (+/-)- 2,4,5-tri-O-benzyl-myo-Inositol with bis(2-cyanoethyl)chlorophosphine gave, after oxidation followed by basic hydrolysis and subsequently hydrogenolysis, (+/-)-myo-Inositol 1,3,4-triphosphate.
- Dreef, C. E.,Marel, G. A. van der,Boom, J. H. van
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p. 161 - 162
(2007/10/02)
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