Myo-inositol 2,4,5-triphosphate

Inositol L-form 1,2,3,5-Tetra-O-angeloyl, 1-28 -Inositol L-form 1,2,4,5-Tetra-O-angeloyl, 1-28 -Inositol l,2 3,4-Di-0-cyclohexylidene, 5-benzoyl, 1-30 wyo-Inositol 1,4-Diphosphate, 1-32 wyo-Inositol 1-0-p-D-Glucopyranoside, nona-Me, 1-32 wyo-Inositol hexakis(phosphate), 1-32 wyo-Inositol monoorthoformate, 1-32 wyo-Inositol 1,2,3,4,5-Pentaphosphate, 1-32 wyo-Inositol 1,2,3,4,6-Pentaphosphate, 1-32 myo-Inositol 1,2,3,5,6-Pentaphosphate, 1-32 myo-Inositol 1,2,4,5,6-Pentaphosphate, 1-32 myo-Inositol 1,3,4,5,6-Pentaphosphate, 1-32 myo-Inositol 2,3,4,5,6-Pentaphosphate, 1-32 myo-Inositol 1-Phosphate, ( ), 1-32 myo-Inositol 4-Phosphate, ( ), 1-32 myo-Inositol 1-Phosphate, 1-32 myo-Inositol 2-Phosphate, 1-32 myo-Inositol 3-Phosphate, 1-32 myo-Inositol 4-Phosphate, 1-32 myo-Inositol 5-Phosphate, 1-32 myo-Inositol 6-Phosphate, 1-32 myo-Inositol 3,4,5,6-Tetra-Ac, 1-32 myo-Inositol 2,3,5,6-Tetrabenzyl, 1-32 myo-Inositol 1,3,4,5-Tetraphosphate, 1-32 myo-Inositol 1,3,5,6-Tetraphosphate, 1-32 myo-Inositol 1,4,5,6-Tetraphosphate, 1-32 myo-Inositol 3,4,5,6-Tetraphosphate, 1-32 myo-Inositol 2,4,6-TVibenzyl, 1,3,5-0-methylidyne, 1-32 myo-Inositol 2,3,5-Tribenzyl, 1-32 myo-Inositol 1,2,3-Triphosphate, 1-32 myo-Inositol 1,3,4-Triphosphate, 1-32 myo-Inositol 1,4,5-Triphosphate, 1-32 myo-Inositol 1,4,6-Triphosphate, 1-32 myo-Inositol 2,4,5-Triphosphate, 1-32 myo -Inositol-1,2,6-triphosphate, 1-32 fl//o-Inositol, 1-27 i -Inositol, 1-28 /-Inositol, 1-28 cw-Inositol, 1-29 ep/-Inositol, 1-30 mwco-Inositol, 1-31... 

The syntheses of racemic myo-inositol 1,4,5-triphosphate and 1,4-bisphosphate by standard processes involving isopropylidene acetals as well as the syntheses of [ H]-D-3-azido-3-deoxy-iiiyo-inositol and D-3-azido-3-deoxy-myo-inositol 2,4,5-triphosphate have been reported. 

A new route to D- and L-myo-inositol 2,4,5-triphosphates from D- and L-chiro-inositol derivatives by inversion of an axial OH group has been achieved. (See Vol. 23, Ref. 69, p.l86 for earlier work.) Also reported is a synthesis of D-c/ >o-inositol 1,3,4-triphosphate. 

Two routes to 1,2-trans-configurated glycosyl phosphonates have been explored. The key-steps involved were the nucleophilic opening of the D-galactal-derived epoxide 54 with dimethyl(trimethylsilyl) phosphite, as shown in Scheme 7, and trimethylsilyl triflate-ptomoted displacement of anomeric acetate by trimethyl phosphite. Phosphonate 55 was further transformed, in eight steps and moderate overall yield, to the monophosphate-bisphosphonate 56, an analogue of myo-inositol 2,4,5-triphosphate. ... 

The preparation of inositol and structurally related phosphates continues to be actively explored. Examples include the first total synthesis of the inositol tetraphosphate enantiomeric pair, Ins(l,2,3,4)P4 (27) and Ins(l,2,3,6)P4 (28). Compounds (27) and (28) were dephosphorylated by a number of different enzymes and thus provide routes to specific inositol triphosphates. A number of myo-inositol 1,4,5-triphosphates, e.g. (29)-(32), modified at the 6-position have been prepared. All such derivatives investigated showed poor affinity for Ins(l,4,5)P3 receptors. A new and comparatively convenient synthesis of I-d-6-0-(2-amino-2-deoxy-a-D-glycopyranosyl)-chiro-inositol 1-phosphate (33) and the corresponding 1,2-cyclic phosphate (34) has been reported. The first examples of poly(ethylene glycol)-linked dimers (35) of D-myo-inositol 1,4,5-triphosphate have been prepared as probes for multi-subunit binding proteins for... 

Mvo-inositol 1,4-diphosphate (38), the racemate of a metabolite of second messenger myo-inositol 1,4,5-triphosphate and its diphosphorothioate analogue (39) have been synthesised from f 1 -1 2.4 S-di-O-isopropylidene-mvo-inositol by way of phosphite intermediates. Similarly, (-mvo-inositol 1,3,4-triphosphate has been obtained from f W2.4.S-tri-O-benzyl-myo-inositol Phosphite chemistry was also employed in the preparation of diphosphorylated and diphosphonylated Lipid A monosaccharide analogues (40). Related Lipid A components are mentioned in Chapter 9. Methyl 3-deoxv-a-D-manno-oct-2-ulopyranosidonic acid 4-phosphate has been synthesised and its chemical stability studied. ... 

The resolution of D,L-2-deoxy-2,2-difluoro-myo-inositol (l,4,5)-triphosphate with S(-)-camphanic acid chloride has been described." The D-enantiomer is a good analogue of Ins(l,4,5)P3 and a substrate for Ins(l,4,5)P3-5-phosphatase and 3-kinase. 

Fundamentally, the Michaelis-Becker reaction, and the first step in the mechanism of the Arbuzov reaction, involves 8 2 substitution at the carbon atom and as such should lead to stereospecific formation of the C—P bond (with inversion of configuration at the carbon atom) when chiral alkyl halides are used. Secondary alkyl halides, in most cases, favor elimination instead of substitution, in contrast to epoxides that react with phosphorus nucleophiles without elimination and with excellent stereoselectivity. The later reaction was successfiiUy used in a synthesis of glycosylphosphonate analog 3 of T>-myo-inositol-1,4,5-triphosphate (Scheme 47.2). ... 

Arg ]-vasopressin stimulated surfactant secretion in primary cultures of rat type 2 pneumocytes independently of adenosine 3 ,5 -cyclic monophosphate (Brown and Wood 1989). A 50% loss of tritiated phosphatidyhnsositol 4,5-biphosphate (PIP2) occurred from cells prelabeled with myo[ H]inositol within 15 s (Brown and Chen 1990). Consistent with vasopressin-induced PIP2 hydrolysis the two breakdown products, 1,2-diacylglycerol and inositol 1,4,5-triphosphate, was observed. Vasopressin stimulated protein kinase C activity twofold over the basal activity of 0.7410.07 nM/min x mg protein. The [Arg ]-vasopressin antagonist, 1-deamino-8-D-arginine vasopressin, inhibited [Arg ]-vasopressin activation of protein kinase C. 

The preparations of 5-deoxy-5-fluoro-myo-inositol, iL-l-deoxy-l-fluoro-myo-inositol, 1d-4-deoxy-4-fluoro-myo-inositol, lL-4-deoxy-4-fluoro-/nyo-inositol, and 2-deoxy-2-fluoro-ffiyo-inositol by conventional chemistry from known racemic /nyo-inositol derivatives and resolution by use of (SH-)-camphamic acid have been described. In a similar way the nthesis of 1-deoxy-l-fluoro-scyWo-inositol, 2-deoxy-2,2-difluoro-my< -inositol, D,L-2-deoxy-2-fluoro-scy/Zo-inositol 1,4,5-triphosphate and D -2-deoxy-2,2-difluoro-ffi) o-inositol 1,4,5-triphosphate have been described. The synthesis of silyl protected myo-inositols with free hydroxyls at 1-, 5-, 6-, 1,4-, 4,5-, 5,6-, 1,4,5-, and 1,4,6-positions has been described. ... 

A full account of an earlier paper (Vol. 25, p. 217, ref. 125) on the preparation of iL-chiro-inositol 2,3,5-triphosphate from L-quebrachitol and the synthesis of L-chiro-inoatol 1,4,6-triphosphate and the corresponding triphosphorothioate also from L-quebrachitol has been reported. Also, a full account (Vol. 23, p. 186, ref 70) on the preparation of racemic /nyo-inoatol 1,4,5 triphosphate and 1,4-bisphosphate-5-phosphorothioate has been reported as well as the preparation of phosphorylated intermediates for the nthesis of both chiral and racemic myo-inoatol 1,43-triphosphate and its phosphorothioate analogue. ... 

The pH optimum for hydrolysis by the major acid phosphatase (EC 3.1.3.2) associated with the aleurone particle of rice grains Oryza sativa Japonica cv. Koshihikari) was 4.8 (Yamagata et al., 1980). The values were respectively 1.74 mM for para-nitrophenyl phosphate and 5.26 mM for adenosine triphosphate. They decreased slightly with an increase in the number of phosphate groups of various inositol phosphates, being 0.43 and 11.76 mM for myoinositol hexakisphosphate and myo-inositol monophosphate, respectively. In addition, the 17 values for myo-inositol bis- and tri-sphosphate were high (564-611 pmol phos-phate/min/mg protein). 

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