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CH2OH

hyde group results in the formation of D-glucofuranose, a hemiacetal containing a five-member ring. Although all three forms of D-glucose exist in biological systems, the pyranose form is by far the most abundant.

Many biologically important sugars are six-carbon sugars that are structurally related to D-glucose (Figure 2-16b). Mannose is identical with glucose except that the orientation of the groups bonded to carbon 2 is reversed. Similarly, galactose, another hexose, differs from glucose only in the orientation of the groups attached to carbon 4. Interconversion of glucose and mannose or galactose requires the breaking and making of covalent bonds; such reactions are carried out by enzymes called epimerases.

The pyranose ring in Figure 2-16a is depicted as planar. In fact, because of the tetrahedral geometry around carbon atoms, the most stable conformation of a pyranose ring has a nonplanar, chairlike shape. In this conformation, each bond from a ring carbon to a nonring atom (e.g., H or O) is either nearly perpendicular to the ring, referred to as axial (a), or nearly in the plane of the ring, referred to as equatorial (e):

Pyranoses

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