68738-29-4Relevant academic research and scientific papers
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.
Flexible stereo- and regioselective synthesis of myo-inositol phosphates (Part 2): Via nonsymmetrical conduritol B derivatives
Podeschwa, Michael A. L.,Plettenburg, Oliver,Altenbach, Hans-Josef
, p. 3116 - 3127 (2007/10/03)
A practical route is described for the preparation of myo-inositol phosphates. Optically pure compounds can be prepared, in both forms, from p-benzoquinone by enzymatic resolution of a diacetoxyconduritol key intermediate. Monosubstituted inositol derivat
Stereoselective oxidation of protected inositol derivatives catalyzed by inositol dehydrogenase from Bacillus subtilis
Daniellou, Richard,Phenix, Christopher P.,Tam, Pui Hang,Laliberte, Michael C.,Palmer, David R. J.
, p. 401 - 403 (2007/10/03)
Inositol dehydrogenase (EC 1.1.1.18) from Bacillus subtilis is shown to have a nonpolar cavity adjacent to the active site, allowing racemic protected inositol derivatives such as 4-O-benzyl-myo-inositol to be recognized with very high apparent stereoselectivity.
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 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
SYNTHESIS OF SOME BENZYL AND METHYL ETHERS OF myo-INOSITOL
Garegg, Per J.,Lindberg, Bengt,Kvarnstroem, Ingemar,Svensson, Stefan C. T.
, p. 205 - 216 (2007/10/02)
The 1D and 1L forms of 1,2,4,5,6- and 1,2,3,4,5-penta-O-methyl-myo-inositol have been prepared from the corresponding chiral mono-O-benzyl derivatives.Convenient preparations are also described of achiral derivatives of 1-, 2-, 4-, and 5-O-benzyl-myo-inos
The Allyl Group for Protection in Carbohydrate Chemistry. Part 18. Allyl and Benzyl Ethers of myo-Inositol. Intermediates for the Synthesis of myo-Inositol Triphosphates
Gigg, Jill,Gigg, Roy,Payne, Sheila,Conant, Robert
, p. 423 - 430 (2007/10/02)
Racemic 1,2:4,5-di-O-isopropylidene-myo-inositol was converted into racemic 1,2,4-tri-O-benzyl-myo-inositol, 1,2,4-tri-O-p-methoxybenzyl-myo-inositol and 2,4,5-tri-O-benzyl-myo-inositol using allyl groups for 'temporary' protection.The benzyl ethers are required as intermediates for the synthesis of the 'second messenger', inositol 1,4,5-triphosphate and its metabolite, inositol 1,3,4-triphosphate. 1,2,3,4-Tetra-O-benzyl-myo-inositol, and its two monoallyl and monoprop-1-enyl ethers, were also prepared as model compounds for phosphorylation studies of the vicinal 5,6-diol system which occurs in 1,2,4-tri-O-benzyl-myo-inositol.
