16006-20-5Relevant academic research and scientific papers
Synthesis of unsymmetric diphospho-inositol polyphosphates
Capolicchio, Samanta,Thakor, Divyeshsinh T.,Linden, Anthony,Jessen, Henning J.
, p. 6912 - 6916 (2013/07/26)
One to rule them all: A novel C2-symmetric phosphoramidite was developed that can be used to prepare all four unsymmetric diphospho inositol pentaphosphates (PP-InsP5). The target structures were synthesized in few steps and high enantiomeric ratios. With the obtained compounds, specificity of Ddp1 from yeast (a PP-InsP5 phosphatase) was studied. Copyright
Enantiodivergence in small-molecule catalysis of asymmetric phosphorylation: Concise total syntheses of the enantiomeric D-myo-inositol-1-phosphate and D-myo-inositol-3-phosphate
Sculimbrene, Bianca R.,Morgan, Adam J.,Miller, Scott J.
, p. 11653 - 11656 (2007/10/03)
Peptide-based catalysts have been found that catalyze the enantiodivergent phosphorylation of a meso myo-inositol-derived triol (1). The sequential screening of random peptide libraries, followed by the evaluation of a focused library, led to the identifi
Structure of (±)-1,2;4,5-di-o-cyclohexylidene myo-inositol and synthesis of myo-inositol 3-phosphate via its phosphorylation with (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one
Spiers, Ian D.,Schwalbe, Carl H.,Blake, Alexander J.,Solomons, Kevin R.H.,Freeman, Sally
, p. 43 - 51 (2007/10/03)
The crystal structure of (±)-1,2;4,5-di-O-cyclohexylidene myo-inositol, refined to R = 2.9%, shows interestingly disordered (flip-flop) hydrogen bonding. The higher reactivity of the 1/3 positions (rather than 4/6) has been evaluated using semi-empirical calculations. This diol has been phosphorylated with (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2- oxazaphospholidin-2-one and the diastereoisomer derived from phosphorylation at the 3-position was isolated by crystallisation. Deprotection with TFA/H2O then H2/Pd-C afforded myo-inositol 3-phosphate in only four steps from myo- inositol.
A simple synthesis of D-myo-inositol 4-phosphate and D-myo- inositol 6-phosphate
Iacobucci,D'Alarcao
, p. 809 - 817 (2007/10/02)
A simple synthesis of the title compounds from myo-inositol is reported. The procedure involves the regioselective dibutyltin oxide-promoted acylation of racemic 1,2:5,6-dicyclohexylidene-myo- inositol (2) with 1-(S)-(-)-camphanyl chloride followed by chr
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 (2007/10/02)
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.
INVESTIGATIONS IN THE FIELD OF DERIVATIVES OF ASYMMETRICALLY SUBSTITUTED MYOINOSITOL. XXVIII. METHODS FOR SYNTHESIS OF TRIPHOSPHOINOSITIDE
Krylova, V. N.,Gornaeva, N. P.,Oleinik, G. F.,Shvets, V. I.
, p. 277 - 283 (2007/10/02)
One of the problems in the synthesis of triphosphoinositides, i.e., the problem of creating their 4,5-diphosphate structure, was investigated.The most effective method of exhaustive phosphorylation of 1(3),2-O-cyclohexylidene-3(1),6(4),di-O-benzyl-sn-myoi
