Meso- Inositol- 1-phosphate

For all the substrates discussed so far the peptide catalysts employed had to differentiate between enantiomeric substrate molecules. Miller et al. subsequently screened peptide libraries for members able to selectively functionalize enantio-topic hydroxyl groups of meso inositols. In particular, they were able to convert myo-inositol 35 to either monophosphorylated D-myo-inositol-l-phosphate 37 or d-myo-inositol-3-phosphate ent-37 in high yield and excellent ee (98% Scheme 12.18) [38, 39], This remarkable result was achieved by use of either of the penta-... 

The myo-isomer is the most abundant form in nature. It occupies a unique place in inositol metabolism because this is the only isomer synthesized de novo from D-glucose-6-phosphate all other isomers are derived from myo-inositol (Loewus, 1990b Loewus and Murthy, 2000). In early 1900s, myo-inositol was called meso-inositol (abbreviated ms-inositol) probably because, like mesotar-taric acid, it does not exhibit optical activity and cannot be resolved into optical isomers (Posternak, 1965). However, as discussed above, six other isomers also do not exhibit optical activity so the name seemed inappropriate. In 1954, the name myo-inositol was introduced - a name not particularly well coined either since it is a pleonasm - both myo and inositol mean muscle. Nevertheless, the name persists. 

In its meso-configuration, inositol can be phosphorylated. Corresponding procedures for the separation and determination of various inositol phosphates were introduced by Smith and MacQuarrie [162]. 

Miller has reported a minimal kinase for the phosphorylative enantioselective desymmetrization of a meio-inositol derivative. Peptide 132, identihed from a small library, provided the highest selectivity using the meso-tno 130 as substrate. This approach was applied to a hve-step synthesis of D-myoinositol-1-phosphate from readily available myoinositol ... 

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