Metabolism of Inositol 

 o 



IV XIV XII 



Pt, Hi 



D-inositol (XII). The deoxyinositol derivative was not attacked more 

 rapidly than the D-inositol derivative in which all hydroxyl groups are 

 in trans position. The oxidation product of XV was therefore identi- 

 fied as D-2,3-diketo-4-deoxy-e?n-inositol (XVI), in which the three 

 adjacent hydroxyl groups are in trans position. 8 



o, 



x = 



A. suboxydans 



xv XVI 



The action of A. suboxydans on these cyclitols seemed at first to fit 

 no easily discernible pattern. In the case of the inositol isomers, one 

 hydroxyl group of a pair of adjacent cis hydroxyls had been attacked, 

 suggesting a specificity of oxidation similar to the one found in 

 straight-chain compounds, but the oxidation of the hydroxyl group on 

 carbon 3 of L-2-deoxy-mwco-inositol (XV) was totally unexpected. 

 However, it must be borne in mind that the structural formulas (Fig. 1) 

 do not describe the actual position of the hydroxyl groups in space but 

 represent merely planar projections based on the conventions intro- 

 duced into stereochemistry by Emil Fischer. It had long been known 

 that the cyclohexane molecule was not planar but could exist as a 

 strainless ring in the "boat" and "chair" forms; later evidence ob- 

 tained in studies using electron diffraction and infrared spectroscopy 

 had led to the recognition of the chair form as the stable conformation 

 of the cyclohexane ring (Fig. 2) . Inspection of a model of cyclohexane 



