Cyclitols nomenclature

Structural formulae have been given for most of the compounds discussed in the text and the major change in nomenclature which has been utilised concerns the numbering of the ring systems of both (—)-shikimic acid and (—)-quinic add. Revised systems of numeration have been employed for these compounds to accord respectively with normal lUPAC procedures and with the tentative rules for cyclitol nomenclature (lUPAC information bulletin. No. 32, 1968 European J. Biochem., 1968, 5, 1). 

Until some uniform configurational nomenclature for cyclitols has been generally accepted, it would appear safer for authors in this field to specify the nomenclature used in every article, or to indicate configurations by means of formulas. 

Note. Cyclitols are generally not regarded as carbohydrates. Their nomenclature is dealt with in other recommendations [8,9],... 

Since the new IUPAC recommendations [5], the nomenclature of quinic acid isomers is very confusing in the literature. Therefore, the latest IUPAC nomenclature is used throughout this paper instead of the older, but still useful, nomenclature. In the IUPAC nomenclature quinic acid is now treated as cyclitol. In the preferred configuration, the carboxy group and the C-4 and C-5 hydroxy groups are equatorial, with the C-l and C-3 hydroxy groups are axial. In the IUPAC system, the former 3-O-acylquinic acids are now renamed 5-O-compounds, and the... 

Nomenclature of Phosphorus-Containing Compounds of Biochemical Importance http //www.chem.qmul.ac.uk/iupac/misc/phospho.htmt Numbering of atoms in Myo-inositol http //www.chem.qmul.ac.uk/iupac/cyclitol/ myo.html... 

The nomenclature of the cyclitols is in a confused state. The peculiar problems associated with the naming and numbering of polysubstituted... 

IUPAC Commission on the Nomenclature of Organic Chemistry and IUPAC-IUB Commission on Biochemical Nomenclature, 1976, Nomenclature of cyclitols. Biochem. J. 153 23-31. 

From the lUPAC-IUB 1973 Recommendations for the Nomenclature of Cyclitols Biochem. J., 153, 23-31, 1976 based upon proposals first issued in 1967 Biochem. /., 112, 17-28, 1969.)... 

The very widespread occurrence of meso-inositol (m. p. 225°) in both plant and animal sources makes this substance by far the most extensively investigated of the cylitols in fact, the comparative rarity of the other inositols has justified the general retention of the name inositol to denote meso-inositol although, as pointed out above, the term has been extended to its isomers, meso-inositol and the equally common name, inactive inositol, are obviously poor names for this compound since six of the other inositols are also optically inactive. The sole attempt at a rigorous systematic nomenclature for the cyclitols is that of Maquenne who suggested the use of a fraction to denote the positions of the hydroxyl... 

It is very difficult to foresee in what direction the future work of the Commission for Nomenclature of Biochemistry will be oriented. It can be assumed, however, that while continuing the study of the nomenclature of the vitamins and steroids, the commission will also start considering other limited groups of compounds carbohydrates, cyclitols, and enzymes. Projects for their nomenclature have appeared in different periodicals. 

Cyclic polyalcohols (or cyclitols , according to the nomenclature of sugar alcohols) also exhibit a very low affinity. The most important representative of this class of compounds is inositol,... 

IUPAC-IUBMB Nomenclature of Carbohydrates,1"Adv. Carbohydr. Chem. Biochem., 52 (1997) 43-177 see also Nomenclature of Cyclitols, Eur. J. Biochem., 57 (1975) 1-7. 

International Union of Pure and Applied Chemistry, and International Union of Biochemistry. Nomenclature of Cyclitols, Recommendations 1973 . Eur. J. Biochem.1975, 57, 1-7. 

Cyclitols are polyhydroxycycloalkanes and -alkenes. The most abundant of these carbocyclic compounds are the hexahydroxycyclohexanes, commonly called inositols, and their methyl ethers. The nomenclature of cyclitols is problematic several systems have been proposed and used. The rules used here are those of lUPAC and lUB (97). 

The numeration of the ring carbon atoms in both (—)-shikimic acid and (—)-quinic acid has been revised to accord with lUPAC nomenclature rules. Thus (—)-shikimic acid is numbered through the double bond and (—)-quinic acid is numbered according to the tentative rules for the nomenclature of cyclitols European J. Biochem., 1968, 5, 1-12). Both of these forms of numeration conflict with earlier forms established by usage in the chemical and biochemical literature. 

Some uncertainty surrounds the nomenclature of (—)-quinic acid and the proposar of the lUPAC-IUB commissions on the nomenclature of Organic Chemistry and Biochemistry that it should be named according to the rules and procedures recommended for cyclitols has not met with universal acceptance . Nevertheless they have been adopted here and are briefly outlined below. 

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