- Synthesis of unsymmetric diphospho-inositol polyphosphates
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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
- Capolicchio, Samanta,Thakor, Divyeshsinh T.,Linden, Anthony,Jessen, Henning J.
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p. 6912 - 6916
(2013/07/26)
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- 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
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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
- Sculimbrene, Bianca R.,Morgan, Adam J.,Miller, Scott J.
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p. 11653 - 11656
(2007/10/03)
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- 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
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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.
- Spiers, Ian D.,Schwalbe, Carl H.,Blake, Alexander J.,Solomons, Kevin R.H.,Freeman, Sally
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- A simple synthesis of D-myo-inositol 4-phosphate and D-myo- inositol 6-phosphate
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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
- Iacobucci,D'Alarcao
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p. 809 - 817
(2007/10/02)
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- 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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- INVESTIGATIONS IN THE FIELD OF DERIVATIVES OF ASYMMETRICALLY SUBSTITUTED MYOINOSITOL. XXVIII. METHODS FOR SYNTHESIS OF TRIPHOSPHOINOSITIDE
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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
- Krylova, V. N.,Gornaeva, N. P.,Oleinik, G. F.,Shvets, V. I.
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p. 277 - 283
(2007/10/02)
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