Haworth ring formulae, monosaccharides

The Haworth representation implies a planar ring. However, monosaccharides assume conformations that are not planar these may be represented by Haworth conformational formulae. The nomenclature of conformations is described in 2-Carb-7. For example, (5-D-glucopyranose assumes a chair conformation ... 

The Haworth projection formulas are neater ways of writing the ring forms shown in the equilibria above and yet preserving the configuration shown at each chiral carbon. It is not difficult to translate the open-chain structure for a monosaccharide into the Haworth ring structure. 

CONFORMATIONAL STRUCTURES Although Haworth projection formulas are often used to represent carbohydrate structure, they are oversimplifications. Bond angle analysis and X-ray analysis demonstrate that conformational formulas are more accurate representations of monosaccharide structure (Figure 7.10). Conformational structures are more accurate because they illustrate the puckered nature of sugar rings. 

Comment Often it is more convenient as well as more acciurate to represent the cyclic forms of the monosaccharides by a ring diagram. Such a representation is the widely used Haworth perspective formula. 

Haworth formulas are a useful way of representing the cyclic forms of monosaccharides. The rings are depicted as flat, with hydroxyl groups or other substituents above or below the ring plane. 

Haworth formulas are named after the English chemist W. N. Haworth (University of Birmingham), who, in 1926, along with E. L. Hirst, demonstrated that the cyclic form of glucose acetals consists of a six-membered ring. Haworth received the Nobel Prize for his work in carbohydrate chemistry in 1937. For an excellent discussion of Haworth formulas and their relation to open-chain forms, see The Conversion of Open Chain Structures of Monosaccharides into the Corresponding Haworth Formulas, Wheeler, D. M. S., Wheeler, M. M., and Wheeler, T. S.,J. Chem. Educ. 1982, 59, 969-970. 

---