I. NOMENCLATURE AND FORMULA 327 



Posternak/' since it could be selectively reduced to either scyllitol or 

 meso-inositol (w?/o-ino&itol) . 



Nitric acid oxidation of w?/o-inositol produces a monoketoinositol which 

 is a racemic mixture of XIII and XIV. Posternak^^ resolved this mix- 

 ture and demonstrated that the levorotatory isomer had structure XIV. 

 Although this compound was obtained from w^o-inositol, according to 

 rule 3 it must be assigned the trivial name of the inositol in which the 

 hydroxyl on carbons 1, 2, 3, 4, and 5 are cis, i.e., ep2-inositol. By rule 2, 

 structure XIV is placed in the d configurational series, and the exact name 

 is therefore D-2-keto-epz-inositol or D-epi-inosose-2. The enantiomorphic 

 XIII is L-2-keto-epz-inositol or L-ept-inosose-2. 



The diketoinositol shown in formula XV is related to both inyo-and muco- 

 inositols (but not to either d- or L-inositol, because these have fewer cis- 

 hydroxyl groups — see rule 3). Since the substituents cis to the hydroxyl on 

 carbon 1 in mi/o-inositol have a numbering sequence (1, 2, 3, 5) lower than 

 that in mwco-inositol (1, 2, 4, 5), the compound is correctly named 1,3- 

 diketo-w?/o-inositol . 



not 



XV XVI-a XVI-6 



1 ,3-Diketo-m2/o- 1 ,5-Diketo-??iMCo- 



inositol inositol 



Aminodesoxyinositols. Several derivatives of inositol in which amino 

 groups replace hydroxyl groups have been prepared synthetically,^*"^^ and 

 at least one, streptamine, is known to occur naturally. Carter and his co- 

 workers^^ have coined the term inosamine as a generic designation for this 

 class of substance, and other authors^^- ^^ have continued the usage. The 

 two monoaminodesoxyinositols derivable from 2-keto-m^?/o-inositol (XII) 

 have been synthesized^^- ^^ and their configurations established^^' ^^' ^^ as 

 XVII and XVIII. Each of these meso structures may readily be named 



13 T. Posternak, Helv. Chim. Acta 25, 746 (1942). 



1* T. Posternak, Helv. Chim. Acta 29, 1991 (1946). 



16 J. Grosheintz and H. O. L. Fischer, J. Am. Chem. Soc. 70, 1479 (1948). 



16 H. E. Carter, R. K. Clark, Jr., B. Lytle, and G. E. McCasland, J. Biol. Chem.. 175, 



683 (1948). 

 " E. May and E. Mosettig, J. Org. Chem. 14, 1137 (1949). 

 i«L. Anderson and H. A. Lardy, /. Am. Chem. Soc. 72, 3141 (1950). 

 19 T. Posternak, Helv. Chim. Acta 33, 1597 (1950). 

 " G. E. McCasland, J. Am. Chem. Soc. 73, 2295 (1951). 



