326 INOSITOLS 



of the two structures in question are : 



5 H 



6 HO 



OPO3— 



1 O3PO 



X=L XI=D 



Thus X would be named L-m^/o-inositol-l-phosphate, and XI would be d- 

 m?/o-inositol-l-phosphate. 



Rule 3. When an inositol derivative contains less than six asymmetric 

 carbon atoms, the compound will he given the trivial name of one of the parent 

 inositols to which it is related, the choice being that parent inositol which has 

 the maximum number of cis-hydroxyl groups. Where this offers more than one 

 possibihty, as in the diketoinositols, the following also apply. Secondarily, 

 the parent inositol chosen is that which has the lowest possible number for its 

 substituents cis to the hydroxyl on carbon 1, or, finally, that which would 

 confer the lowest possible numbering on substituents other than hydroxyl. 



This rule may be illustrated by its application to the ketoinositols 

 (named inososes by Posternak^) obtainable by oxidation of w^/o-inositol. 



O 



I 



XII 



2-Keto-'/?iyo-inositol 

 (r?J2/o-Inosose-2) 



XIII 



L-2-Keto-epwnositol 

 (L-ciDi-Inosose-2) 



XIV 



D-2-Keto-epi-inositol 

 (D-epz-Inosose-2) 



The bacterium Acetobacter suboxydans oxidizes m?/o-inositoP^ • ^^ to a mono- 

 ketoinositol which was shown by Posternak^^ to have the structure XII. 

 This compound (XII) has three hydroxyl groups projecting upward and 

 only two projecting downward. Hence, according to rule 3 it receives the 

 trivial name of m?/o-inositol which has an hydroxyl group projecting upward 

 in position 2. The name of choice for XII is therefore 2-keto-m?/o-inositol 

 or w?/o-inosose-2. It had previously been named sc?/ZZo-meso-inosose by 



" A. J. Kluyver and A. G. J. Boezaardt, Rec. trav. chim. 58, 956 (1939). 

 12 H. E. Carter, C. Belinsky, R. K. Clark, Jr., E. H. Flynn, B. Lytle, G. E. McCas- 

 land, and M. Robbins, J. Biol. Chem. 174, 415 (1948). 



